U.S. patent application number 09/994449 was filed with the patent office on 2002-08-22 for method of preparing an organosilicon compound containing a methacryloxy functional group.
Invention is credited to Shirahata, Akihiko, Wakita, Keiji.
Application Number | 20020115878 09/994449 |
Document ID | / |
Family ID | 18908494 |
Filed Date | 2002-08-22 |
United States Patent
Application |
20020115878 |
Kind Code |
A1 |
Wakita, Keiji ; et
al. |
August 22, 2002 |
METHOD OF PREPARING AN ORGANOSILICON COMPOUND CONTAINING A
METHACRYLOXY FUNCTIONAL GROUP
Abstract
A method of preparing an organosilicon compound containing an
acryloxy-functional group or a methacryloxy-functional group
represented by general formula CH.sub.2.dbd.CR.sup.1--COO
--R.sup.2--Si(OR.sup.3).sub- .nR.sup.4.sub.3-n, where R.sup.1,
R.sup.2, R.sup.3, R.sup.4 are as described below, comprising
reacting (a) an alkali-metal salt of acrylic acid or an
alkali-metal salt of methacrylic acid described by general formula
CH.sub.2.dbd.CR.sup.1COOM.sup.1, where R.sup.1 is a methyl group or
a hydrogen atom and M.sup.1 is an alkali metal and (b) an
organosilicon containing a halogen-substituted organic group
described by general formula
XR.sup.2Si(OR.sup.3).sub.nR.sup.4.sub.3-n, where X is a halogen
atom, R.sup.2 is an alkylenoxyalkylene group or an alkylene group
comprising 1 to 6 carbon atoms, R3 is an alkyl group comprising 1
to 6 carbon atoms or an alkoxyalkyl group comprising 2 to 4 carbon
atoms, R.sup.4 is a monovalent hydrocarbon group, and n is an
integer of 1 to 3; in the presence of (c) a tertiary amine having a
cyclic structure selected from the group consisting of
1,8-diazabicyclo [5.4.0]undec-7-ene, 1,4-diazabicyclo[2.2.2]octane,
and 1,5-diazabicyclo[4.3.0]-non-5-ene.
Inventors: |
Wakita, Keiji; (Chiba
Prefecture, JP) ; Shirahata, Akihiko; (Chiba
Prefecture, JP) |
Correspondence
Address: |
Dow Corning Corporation
Intellectual Property Department
Mail C01232
P. O. Box 994
Midland
MI
48686-0994
US
|
Family ID: |
18908494 |
Appl. No.: |
09/994449 |
Filed: |
November 28, 2001 |
Current U.S.
Class: |
556/440 |
Current CPC
Class: |
C07F 7/1892
20130101 |
Class at
Publication: |
556/440 |
International
Class: |
C07F 007/08 |
Foreign Application Data
Date |
Code |
Application Number |
Feb 22, 2001 |
JP |
2001-46973 |
Claims
We claim:
1. A method of preparing an organosilicon compound containing an
acryloxy-functional group or a methacryloxy-functional group
described by general
formulaCH.sub.2.dbd.CR.sup.1--COO--R.sup.2--Si(OR.sup.3).sub.nR.s-
up.4.sub.3-nwhere R.sup.1, R.sup.2, R.sup.3, R.sup.4 are as
described below, comprising reacting (a) an alkali-metal salt of
acrylic acid or an alkali-metal salt of methacrylic acid described
by general formulaCH.sub.2.dbd.CR.sup.1COOM.sup.1,where R.sup.1 is
a methyl group or a hydrogen atom and M.sup.1 is an alkali metal
and (b) an organosilicon containing a halogen-substituted organic
group described by general
formulaXR.sup.2Si(OR.sup.3).sub.nR.sup.4.sub.3-n, where X is a
halogen atom, R.sup.2 is an alkylenoxyalkylene group or an alkylene
group comprising 1 to 6 carbon atoms, R3 is an alkyl group
comprising 1 to 6 carbon atoms or an alkoxyalkyl group comprising 2
to 4 carbon atoms, R.sup.4 is a monovalent hydrocarbon group, and n
is an integer of 1 to 3; in the presence of (c) a tertiary amine
having a cyclic structure selected from the group consisting of
1,8-diazabicyclo[5.4.0]undec-7-ene, 1,4-diazabicyclo[2.2.2]octane,
and 1,5-diazabicyclo[4.3.0]-non-5-ene.
2. The method of preparing an organosilicon compound containing an
acryloxy-functional group or a methacryloxy-functional group
according to claim 1, where the alkali-metal salt of acrylic acid
or the alkali-metal salt of methacrylic acid of component (a) and
the tertiary amine of component (c) having a cyclic structure are
added in a mole ratio (a) to (c) of 1:0.0001 to 1:0.05.
3. The method of preparing an organosilicon compound containing an
acryloxy-functional group or a methacryloxy-functional group
according to claim 1 where component (b) is selected from the group
consisting of .gamma.-chloropropyltrimethoxysilane and
.gamma.-chloropropylmethyldimeth- oxy silane.
4. The method of preparing an organosilicon compound containing an
acryloxy-functional group or a methacryloxy-functional group
according to claim 2 where component (b) is selected from the group
consisting of .gamma.-chloropropyltrimethoxysilane and
.gamma.-chloropropylmethyldimeth- oxysilane.
5. The method of preparing an organosilicon compound containing an
acryloxy-functional group or a methacryloxy-functional group
according to claim 1 where component (a) is selected from the group
consisting of sodium methacrylate, potassium methacrylate, sodium
acrylate, and potassium acrylate.
6. The method of preparing an organosilicon compound containing an
acryloxy-functional group or a methacryloxy-functional group
according to claim 1 where X is a chlorine or bromine atom.
7. The method of preparing an organosilicon compound containing an
acryloxy-functional group or a methacryloxy-functional group
according to claim 1 where component (c) is
1,8-diazabicylo[5.4.0]undac-7-ene.
8. The method of preparing an organosilicon compound containing an
acryloxy-functional group or a methacryloxy-functional group
according to claim 1 where the mole ratio of component (a) to
component (b) added to the method is 0.1 to 2.
9. The method of preparing an organosilicon compound containing an
acryloxy-functional group or a methacryloxy-functional group
according to claim 1 where the mole ratio of component (a) to
component (b) added to the method is 0.15 to 1.5.
10. The method of preparing an organosilicon compound containing an
acryloxy-functional group or a methacryloxy-functional group
according to claim 1 where the alkali-metal salt of acrylic acid or
the alkali-metal salt of methacrylic acid of component (a) and the
tertiary amine of component (c) having a cyclic structure are added
in a mole ratio (a) to (c) of 1:0.001 to 1:0.01.
Description
FIELD OF THE INVENTION
[0001] The present invention relates to a new method for easily and
efficiently preparing an organosilicon compound containing a
methacryloxy-functional group. This method is based on a reaction
conducted between an alkali-metal salt of a methacrylic acid and an
organosilicon compound with a halogen-substituted organic group in
the presence of a phase-transfer catalyst.
BACKGROUND OF THE INVENTION
[0002] Japanese Patent Publication (Kokoku) S42-23332 discloses a
method of preparing an organosilane compound containing a
methacryloxy group by causing a reaction between a solid alkyl salt
of a methacrylic acid and a chloroalkyl silane of general
formula:
ClCH.sub.2(CH.sub.2).sub.m-1Si(OR.sup.5).sub.nR.sup.6.sub.3-n
[0003] where n is an integer between 1 and 3, m is an integer
between 1 and 4, and R.sup.5 and R.sup.6 are alkyl groups having 1
to 4 carbon atoms, the reaction being carried out in the presence
of a phase-transfer catalyst such as a tertiary amine or a
quaternary ammonium salt.
[0004] In the aforementioned publication, the phase-transfer
catalysts can be represented by triethylamine, dimethyl aniline,
tetramethyl ammonium chloride, benzyltrimethyl ammonium chloride,
etc. However, the use of the above phase-transfer catalysts
requires that the reaction be carried out at a high temperature of
140 to 180.degree. C. and be extended for about 6 ammonium
chloride, etc. However, the use of the above phase-transfer
catalysts requires that the reaction be carried out at a high
temperature of 140 to 180.degree. C. and be extended for about 6
hours. Furthermore, the reaction may require the use of additional
solvents such as dimethylformamide and toluene or xylene. The yield
of the obtained organosilane that contains acryloxy-functional
groups or methacryloxy-functional groups never exceeds 90% and, in
many cases, does not exceed 70%.
[0005] Some publications report successful use of the following
phase-transfer catalysts for the aforementioned reaction: cyclic
polyethers (Japanese Laid-Open Patent Application Kokai S52-73826),
quaternary phosphonium salts (Kokai S56-104890), and quaternary
ammonium salts with a total number of carbon atoms of from 12 to 40
(Kokai H3-209388). However, all of these catalysts are expensive,
have high molecular weight, and in order to achieve high catalytic
efficiency have to be used in large quantities. These conditions
increase the final cost of the resulting organosilane with
acryloxy-functional groups or methacryloxy-functional groups.
[0006] Kokai 5-306290 describes a process which involves the
reaction of an acrylic acid or a methacrylic acid with an
organosilane that contains a halogen-substituted organic group in
the presence of a cyclic tertiary-amine compound. However, since
this reaction utilizes the aforementioned tertiary amine compound
as an adjuvant for hydrogen halide formed in the reaction, the
tertiary amine compound has to be used in a stoichiometric
quantity, i.e., almost in equivalent mole quantity against the
acrylic acid or the methacrylic acid, and the organosilane with
halogen-substituted organic groups. The above condition requires
the use of additional processes for recovery and regeneration of
tertiary amine. Furthermore, quantitative reuse of the tertiary
amine presents a problem, and the process becomes economically
unjustifiable.
[0007] As a result of a study conducted by the present inventors
and aimed at the solution of the problems of the prior art, it has
been found that, if an alkali metal salt of acrylic acid or an
alkali metal salt of methacrylic acid is used as a starting
material, a tertiary amine compound having a cyclic structure
becomes an extremely efficient phase-transfer catalyst. More
specifically, it is an object of the present invention to provide a
method of inexpensive production of an organosilicon compound
containing an acryloxy-functional group or a
methacryloxy-functional group by causing a reaction between an
alkali metal salt of acrylic acid or an alkali metal salt of
methacrylic acid and an organosilicon compound having a
halogen-substituted organic group. The aforementioned
phase-transfer catalyst is a relatively inexpensive compound and is
used in extremely small quantities and the reaction is
characterized by high speed and high yield.
SUMMARY OF THE INVENTION
[0008] The present invention is a method of preparing an
organosilicon compound containing an acryloxy-functional group or a
methacryloxy-functional group represented by general formula
CH.sub.2.dbd.CR.sup.1--COO--R.sup.2--Si(OR.sup.3).sub.nR.sup.4.sub.3-n
[0009] where R.sup.1, R.sup.2, R.sup.3, R.sup.4 are as described
below, the method comprises reacting
[0010] (a) an alkali-metal salt of acrylic acid or an alkali-metal
salt of methacrylic acid described by general formula
CH.sub.2.dbd.CR.sup.1COOM.sup.1,
[0011] where R.sup.1 is a methyl group or a hydrogen atom and Ml is
an alkali metal and
[0012] (b) an organosilicon containing a halogen-substituted
organic group described by general formula
XR.sup.2Si(OR.sup.3).sub.nR.sup.4.sub.3-n,
[0013] where X is a halogen atom, R.sup.2 is an alkylenoxyalkylene
group or an alkylene group comprising 1 to 6 carbon atoms, R3 is an
alkyl group comprising 1 to 6 carbon atoms or an alkoxyalkyl group
comprising 2 to 4 carbon atoms, R4 is a monovalent hydrocarbon
group, and n is an integer of 1 to 3; in the presence of
[0014] (c) a tertiary amine having a cyclic structure selected from
the group consisting of 1,8-diazabicyclo [5.4.0] undec-7-ene,
1,4-diazabicyclo [2.2.2] octane, and 1,5-diazabicyclo
[4.3.0]-non-5-ene.
DESCRIPTION OF THE INVENTION
[0015] The present invention is a method of preparing an
organosilicon compound containing an acryloxy-functional group or a
methacryloxy-functional group represented by general formula
CH.sub.2.dbd.CR.sup.1--COO--R.sup.2--Si(OR.sup.3).sub.nR.sup.4.sub.3-n
[0016] where R.sup.1, R.sup.2, R.sup.3, R.sup.4 are as described
below, the method comprises reacting
[0017] (a) an alkali-metal salt of acrylic acid or an alkali-metal
salt of methacrylic acid described by general formula
CH.sub.2--CR.sup.1COOM.sup.1,
[0018] where R.sup.1 is a methyl group or a hydrogen atom and
M.sup.1 is an alkali metal and
[0019] (b) an organosilicon containing a halogen-substituted
organic group described by general formula
XR.sup.2Si(OR.sup.3).sub.nR.sup.4.sub.3-n,
[0020] where X is a halogen atom, R2 is an alkylenoxyalkylene group
or an alkylene group comprising 1 to 6 carbon atoms, R3 is an alkyl
group comprising 1 to 6 carbon atoms or an alkoxyalkyl group
comprising 2 to 4 carbon atoms, R.sup.4 is a monovalent hydrocarbon
group, and n is an integer of 1 to 3; in the presence of
[0021] (c) a tertiary amine having a cyclic structure selected from
the group consisting of 1,8-diazabicyclo [5.4.0] undec-7-ene,
1,4-diazabicyclo [2.2.2] octane, and 1,5-diazabicyclo
[4.3.0]-non-5-ene.
[0022] Component (a) of the present invention is an alkali-metal
salt of acrylic acid or an alkali-metal salt of methacrylic acid
described by general formula
CH.sub.2.dbd.CR.sup.1COOM.sup.1,
[0023] where R.sup.1 is a methyl group or a hydrogen atom and
M.sup.1 is an alkali metal. Component (a) is represented by the
following specific compounds: sodium methacrylate, potassium
methacrylate, sodium acrylate, and potassium acrylate.
[0024] The aforementioned component (a) can be produced by
neutralizing an acrylic acid or a methacrylic acid with sodium or
potassium hydroxide or by saponifying a methyl acrylate or a methyl
methacrylate with a sodium or potassium hydroxide. The alkali metal
salt of acrylic acid or the alkali metal salt of methacrylic acid
can be used in the reaction in a solid state or in a liquid state
as a dispersion or a solution in an appropriate solvent.
[0025] Component (b) is an organosilicon containing a
halogen-substituted organic group described by general formula
XR.sup.2Si(OR.sup.3).sub.nR.sup.4.sub.3-n,
[0026] where X is a halogen atom, preferably chlorine or bromine.
R.sup.2 is an alkylenoxy-alkylene group or an alkylene group having
1 to 6 carbon atoms. The following are examples of such groups:
methylene, ethylene, methylmethylene, propylene, methylethylene,
butylenes, hexylene, 1-methylpentylene, 1,4-dimethylbutylene, or a
similar alkylene group; methyleneoxypropylene,
methylene-oxypentylene or a similar alkylene-oxyalkylene group.
Most preferable among the above are methylene, propylene,
butylenes, methylene-oxypropylene, and methylene-oxypentylene
groups, and especially propylene groups. R3 is an alkyl group
comprising 1 to 6 carbon atoms or an alkoxyalkyl group having 2 to
4 carbon atoms, R4 is a monovalent hydrocarbon group, and n is an
integer of 1 to 3. The following are examples of alkyl groups
suitable for R.sup.3: methyl, ethyl, propyl, butyl, pentyl,
isopropyl, isobutyl, cyclopentyl, and cyclohexyl groups. Examples
of alkoxyalkyl groups represented by R.sup.3 are methoxyethyl,
methoxypropyl, and methoxybutyl groups. Most preferable of the
above R.sup.3 groups are methyl, ethyl, and methoxyethyl groups.
R.sup.4 is a monovalent hydrocarbon group such as a methyl, ethyl,
propyl, butyl, pentyl, isopropyl, isobutyl, cyclopentyl,
cyclohexyl, or a similar alkyl group; a phenyl, tolyl, xylyl,
naphthyl, or a similar aryl group; a vinyl, allyl, butenyl,
pentenyl, hexenyl, or a similar alkenyl group; a benzyl, phenethyl,
or a similar aralkyl group. Most preferable R.sup.4 is a methyl
group. Subscript "n" is an integer of from 1 to 3.
[0027] It is preferred to use the following organosilicon compounds
having halogen-substituted organic groups:
chloromethyldimethylmethoxysilane,
.gamma.-chloropropyltrimethoxysilane,
.gamma.-chloropropyltris-(methoxyet- hoxy) silane,
.gamma.-chloropropylmethyldimethoxysilane,
.gamma.-chloropropylbutyldimethoxysilane,
.gamma.-chlorobutyltrimethoxysi- lane,
.delta.-chlorobutylmethyldimethoxysilane,
.delta.-chlorobutyl-tris(m- ethoxyethoxy)silane,
.gamma.-bromopropyltrimethoxysilane,
.gamma.-bromopropyltriethoxysilane,
bromopropyltris-(methoxyethoxy)silane- ,
.gamma.-bromopropylmethyldimethoxysilane, or the like. Among these
compounds most preferable are y-chloropropyltrimethoxysilane,
.gamma.-chloropropyltriethoxysilane, .gamma.-chloropropyl
tris-(methoxyethoxy)silane,
.gamma.-chloropropylmethyldimethoxysilane, especially,
.gamma.-chloropropyltrimethoxysilane and
.gamma.chloropropylmethyldimethoxysilane.
[0028] The tertiary amine with a cyclic structure, which
constitutes component (c), is known in the art in various types.
However, the following tertiary amines are preferable for the
present invention: 1,8-diazabicyclo [5.4.0] undec-7-ene,
1,4-diazabicyclo [2.2.2] octane, and 1,5-diazabicyclo
[4.3.0]-non-5-ene. Among these, most suitable is 1,8-diazabicyclo
[5.4.0] undec-7-ene (hereinafter referred to as DBU), as it is
least expensive and is readily available on the market.
[0029] It is recommended that the present reaction be carry out
with the use of components (a) and (b) in an amount of 0.1 to 2
mole, preferably 0.15 to 1.5 mole of the alkali metal salt of
acrylic acid or the alkali metal salt of methacrylic acid
(component (a)), based on 1 mole of the organosilicon that contains
a halogen-substituted organic group (component (b)).
[0030] The tertiary amine (c) with a cyclic structure, which is
used as a phase-transfer catalyst, should be added in an amount of
0.0001 to 0.05 mole, preferably 0.001 to 0.01 mole, based on 1 mole
of the alkali metal salt of acrylic acid or the alkali metal salt
of methacrylic acid (component (a)). The reaction should be carried
out at a temperature of 30.degree. C. to 180.degree. C., preferably
of 80.degree. C. to 130.degree. C. The reaction time may differ
depending on the type of the aforementioned alkali metal salt of
acrylic acid or the alkali metal salt of methacrylic acid, amount
of the catalyst used in the reaction, etc., but normally the
reaction may last from 10 min. to several tens of hours.
[0031] Although there are no specific requirements for the use of a
solvent, the method of the invention can be carried out with a
solvent. In some cases the organosilicon (b) that contains a
halogen-substituted organic group may be used as both a reaction
substrate and a solvent. The solvent can be represented by benzene,
toluene, xylene, or a similar aromatic-type solvent; methanol,
ethanol, or a similar alcohol-type solvent; or methylformamide, or
another solvent neutral to the starting materials and the
catalyst.
[0032] In order to prevent polymerization during the reaction and
distillation, the composition may contain conventional
polymerization inhibitors such as a phenol compound represented by
methoxyphenol and 2,6-di-t-butyl-4-methylphenol, phenothiazine, an
aminetype compound, or a sulfur-containing compound.
[0033] Compounds which contain acryloxy functional groups or
methacryloxy functional groups and are produced by the present
method are described by general formula
CH.sub.2.dbd.CR.sup.1--COO--R.sup.2--Si(OR.sup.3).sub.nR.sup.4.sub.3-n,
[0034] where R.sup.1, R.sup.2, R.sup.3, R.sup.4 are the same as
defined above. The following are examples of such compounds:
methacryloxymethyldimethylmethoxysilane,
.gamma.-methacryloxypropylmethyd- imethoxysilane,
.GAMMA.-methacryloxypropyltrimethoxysilane,
.gamma.-methacryloxypropyltriethoxysilane,
.gamma.-methacryloxypropyl-tri- s-(methoxyethoxy) silane,
.gamma.-methacryloxybutyl dimethoxysilane,
.delta.-methacryloxybutyl trimethoxysilane,
.delta.-methacryloxybutylmeth- yldimethoxysilane,
.delta.-methacryloxybutyltris-(methoxyethoxy)silane;
acryloxymethyldimethylmethoxysilane,
.gamma.-acryloxypropylmethyldimethox- ysilane,
.gamma.acryloxypropyltrimethoxysilane, .gamma.-acryloxypropyltrie-
thoxysilane, .gamma.-acrylopxypropyl-tris(methoxyethoxy)silane,
.gamma.-acryloxypropylbutyldimethoxysilane,
.delta.-acryloxybutyltrimetho- xysilane,
.delta.-acryloxybutylmethyldimethoxysilane,
.delta.-acryloxybutyl-tris(methoxyethoxy)silane, etc.
EXAMPLES
[0035] The invention will be further described with reference to
specific examples, which, however, should not be construed as
limiting the scope of application of the invention.
Practical Example 1.
[0036] A 100-ml three-neck flask equipped with a reflux cooling
tube, stirrer, and thermometer was loaded with 12.4 g (0.1 mole)
potassium methacrylate, 29.8 g (0.15 mole) of
.gamma.-chloropropyltrimethoxysilane, 0.12 g (0.0008 mole) of
1,8-diazabicyclo
[0037] undec-7-ene as catalyst (DBU), and 7 mg of a polymerization
inhibitor in the form of phenothiazine. The components were then
stirred for 2 hours at 105.degree. C. Analysis by gas
chromatography (GC) showed that the reaction produced 23.8 g of
.gamma.-methacryloxypropyltrimethoxy- silane. The yield of the
product was 96% based on potassium methacrylate.
Comparative Example 1.
[0038] A reaction was carried out under the same conditions as in
Practical Example 1, except that 0.15 g (0.0005 mole) of a
quaternary ammonium salt in the form of brominated tetrabutyl
ammonium was used as a catalyst instead of DBU. The yield of
.gamma.-methacryloxypropyltrimethox- ysilane after 2-hour reaction
was 30%, and after 4-hour reaction less than 64%.
Comparative Example 2.
[0039] A reaction was carried out under the same conditions as in
Practical Example 1, except that 0.22 g (0.0005 mole) of a
quaternary ammonium salt in the form of chlorinated trioctyl methyl
ammonium was used as a catalyst instead of DBU. The yield of
.gamma.-methacryloxypropy- ltrimethoxysilane after 2-hour reaction
was 33%, and after 6-hour reaction less than 67%.
Practical Example 2.
[0040] A reaction was carried out similar to Practical Example 1
with the use of 10.8 g (0.1 mole) sodium methacrylate, 29.8 g (0.15
mole) .gamma.-chloropropyl trimethoxysilane, 0.08 g (0.0005 mole)
DBU as a catalyst, 7 mg phenothiazine, and 10 ml toluene for 2
hours at 105.degree. C. Analysis by GC showed that the reaction
produced 23.3 g of .gamma.-methacryloxypropyltrimethoxysilane. The
yield of the product was 94% based on sodium methacrylate.
Comparative Example 3.
[0041] A reaction was carried out under the same conditions as in
Practical Example 2, except that 0.21 g (0.0005 mole) of a
quaternary ammonium salt in the form of chlorinated trioctyl methyl
ammonium was used as a catalyst instead of DBU. The yield of
.gamma.-methacryloxypropy- ltrimethoxysilane after a 2-hour
reaction was 37%, and after 6-hour reaction less than 38%.
Practical Example 3.
[0042] A reaction was carried out under the same conditions as in
Practical Example 1, except that amount of DBU used as a catalyst
was reduced to 0.03 g (0.0002 mole). The yield of
.gamma.-methacryloxypropylt- rimethoxysilane after a 2-hour
reaction was 34%, but after 6 hour reaction reached a high value of
95%.
Practical Example 4.
[0043] A reaction was carried out under the same conditions as in
Practical Example 1, except that 0.06 g (0.0005 mole) of
1.5-diazabicyclo [4.3.0]-non-5-ene were used as a catalyst. The
yield of .gamma.-methacryloxypropyl trimethoxysilane after a 2-hour
reaction was 93%.
Practical Example 5.
[0044] A reaction was carried out similar to Practical Example 1 at
105.degree. C. for 2 hours with a mixture consisting of 12.4 g (0.1
mole) potassium methacrylate, 27.4 g (0.15 mole)
.gamma.-chloropropylmethyldime- thoxysilane, 0.08 g (0.0005 mole)
DBU as a catalyst, and 7 mg phenothiazine as a polymerization
inhibitor. Analysis by GC showed that the reaction produced 22.5 g
of .gamma.-methacryloxypropyl-methyldimethox- ysilane. The yield of
the product was 97% based on potassium methacrylate.
Practical Example 6.
[0045] A reaction was carried out similar to Practical Example 1 at
105.degree. C. for 2 hours with a mixture consisting of 12.4 g (0.1
mole) potassium methacrylate, 36.1 g (0.15 mole)
.gamma.-chloropropyltriethoxys- ilane, 0.08 g (0.0005 mole) DBU as
a catalyst, and 7 mg phenothiazine as a polymerization inhibitor.
Analysis by GC showed that the reaction produced 27.9 g of
.gamma.-methacryloxypropyltriethoxysilane. The yield of the product
was 96% based on potassium methacrylate.
Practical Example 7.
[0046] A reaction was carried out similar to Practical Example 1 at
105.degree. C. for 2 hours with a mixture consisting of 9.4 g (0.1
mole) sodium acrylate, 29.8 g (0.15 mole)
.gamma.-chloropropyltrimethoxysilane, 10 ml toluene, 0.08 g (0.0005
mole) DBU as a catalyst, and 7 mg phenothiazine as a polymerization
inhibitor. Analysis by GC showed that the reaction produced 22.3 g
of .gamma.-acryloxypropyltrimethoxysilane. The yield of the product
was 95% based on sodium acrylate.
* * * * *