Monomer of carbonate ester having isopropenylphenyl group

Polyfunctional monomers are disclosed that yield transparent resins having high transparency and excellent surface hardness and heat resistance. The present polyfunctional monomers are represented by the general formula (I): ##STR1## wherein R represents a group having a carbamido group or an oxazolidone group that will be bonded to the dimethylbenzyl group of the formula (I) and an acryl group or methacryl group at the other end. Control of the polymerization of the polyfunctional monomers is easy, and polymerization of the polyfunctional monomers yield and resins having excellent surface hardness, heat resistance, and workability, and having high transparency. The resins are well adapted for use as glazing materials, optical lenses, and optical disc substrates.

BACKGROUND OF THE INVENTION 
1. Field of the invention 
The present invention relates to novel polyfunctional monomers useful as 
starting material for the production of transparent resins. 
2. Description of the Prior Art 
Transparent resins are generally light in weight and excellent in impact 
resistance, workability, and mass-productivity in comparison to inorganic 
glasses, and are used, for example, as vehicle windows, light-covers, 
indoor notice boards, and skylights. 
The synthetic resins mainly used for these applications are for example, 
polymethyl methacrylate, polystyrene, and polycarbonate, as well as 
polydiethylene glycol bisallyl carbonate. 
The present inventors have investigated the use of transparent resins for 
parts pertaining to vehicle components such as car windows, and have 
discovered that polymethyl methacrylate, polystyrene, and polycarbonate 
have problems in that the surface hardness of these products is low, the 
resin surface is susceptible to marring, and they are poor in heat 
resistance. Accordingly, the present inventors have studied intensively to 
solve these problems. 
SUMMARY OF THE INVENTION 
The present invention overcomes the problems and disadvantages of the prior 
art by providing a new class of monomers from which hard transparent 
resins can be prepared that are not attended by the disadvantages 
discussed above. 
An object of the invention is to provide polyfunctional monomers that can 
be used as starting materials for production of transparent resins having 
high transparency, excellent surface hardness, and heat resistance. 
A further object of the present invention is to provide polyfunctional 
monomers whose polymerization conditions are easy to select. 
A still further object of the invention is to provide a process for 
production of the polyfunctional monomers. 
Additional objects and advantages of the invention will be apparent from 
the description that follows, or may be learned by practicing the 
invention. 
To achieve the objects and in accordance with the purpose of the invention, 
as embodied and broadly described herein, the present invention provides a 
polyfunctional monomer of the general formula (I): 
##STR2## 
wherein R is selected from the group consisting of 
##STR3## 
and wherein R.sub.1 to R.sub.10 each represents hydrogen or a methyl group. 
The present invention also provides a process for producing the 
polyfunctional monomers, comprising reacting 
3-isopropenyl-.alpha.,.alpha.-diemthylbenzyl isocyanate or 
4-isopropyenyl-.alpha.,.alpha.-dimethylbenzyl isocyanate with various 
mono-, di- and tri-acrylate esters, depending on the structure of the 
desired product. 
DETAILED DESCRIPTION OF THE INVENTION 
Reference will now be made in detail to the present preferred embodiments 
of the invention. 
The first group of the present novel polyfunctional monomers comprises a 
difunctional monomer represented by the general formula (II): 
##STR4## 
wherein R.sub.1 and R.sub.2 each represent hydrogen or a methyl group. 
Specific and non-limiting examples thereof include 
N-(3-isopropenyl-.alpha., .alpha.-dimethylbenzyl)-2-acryloyloxyethyl 
methacryloyloxyethyl carbamate, N-(4-isopropenyl-2-methacryloyloxyethyl 
carbamate, 
N-(4-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)-2-acryloyloxyethyl 
carbamate, 
N-(4-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)-2-methacryloyloxyethyl 
carbamate, 
N-(3-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)-1-acryloyloxypropan-2-yl 
carbamate, N-(3-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)-1- 
methacryloyloxypropan-2-yl carbamate, N-(4-isopropenyl-.alpha.,.alpha.- 
dimethylbenzyl)-1-methacryloyloxypropan-2-yl carbamate. 
These compounds can be produced by reacting a compound selected from the 
group consisting of 3-isopropenyl-.alpha.,.alpha.-dimethylbenzyl 
isocyanate and 4-isopropenyl-.alpha.,.alpha.-dimethylbenzyl isocyanate 
with a compound selected from the group consisting of 2-hydroxyethyl 
acrylate, 2-hydroxyethyl methacrylate, 2-hydroxypropyl acrylate and 
2-hydroxypropyl methacrylate. Optionally, the reaction may be conducted in 
a solvent or without solvent and optionally in the presence of a 
urethanization-promoting catalyst. 
The above reaction is carried out such that 1 to 1.2 mol, preferably 1 to 
1.05 mol, of 2-hydroxyethyl acrylate, 2-hydroxyethyl methacrylate, 
2-hydroxypropyl acrylate or 2-hydroxypropyl methacrylate is added to 1 mol 
of 3-isopropenyl-.alpha.,.alpha.-dimethylbenzyl isocyanate or 
4-isopropenyl-.alpha.,.alpha.-dimethylbenzyl isocyanate. Preferably, the 
reaction is carried out in a solvent that will not react with the 
reagents, such as hexane, benzene, or toluene. The reaction temperature is 
kept at from about 25 to about 110.degree. C., preferably from about 
40.degree. to about 65.degree. C., to allow the reaction to proceed. 
Optionally, a urethanization-promoting catalyst such as dibutyl tin 
dilaurate is added in an amount of from about 0.1 to about 5 wt. %, 
preferably from about 0.5 to about 3 wt. %, based on the weight of the 
isocyanate. After the reaction is complete, the reaction medium is 
purified by chromatography to produce a difunctional carbamic acid ester 
according to the present invention. 
The second group of the present novel polyfunctional monomers comprises a 
polyfunctional monomer selected from the group consisting of monomers 
represented by the general formulae (III), (IV) and (V): 
##STR5## 
wherein R.sub.3 and R.sub.4 each represent hydrogen or a methyl 
##STR6## 
wherein R.sub.5 and R.sub.6 each represent hydrogen or a methyl group, and 
##STR7## 
wherein R.sub.7, R.sub.8, and R.sub.9 each represent hydrogen or a methyl 
group. 
Specific and non-limiting examples thereof include 
N-(3-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)-1,3-diacryloyloxypropan2- 
yl carbamate, 
N-(3-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)-1-acryloyloxy-3-methacryl 
oyloxypropan-2-yl carbamate 
N-(3-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)-1,3-dimethacryloyloxyprop 
an2-yl carbamate, N-(4-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)-1 
3-diacryloyloxypropan-2-yl carbamate, 
N-(4-isopropenyl-.alpha.,.alpha.dimethylbenzyl)-1-acryloyloxy-3-methacrylo 
yloxypropan-2-yl carbamate, 
N-(4-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)-1,3-dimethacryloyloxyprop 
an-2-yl carbamate, 
N-(3-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)-2,3-diacryloyloxypropan-1 
-yl carbamate 
N-(3-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)-2-acryloyloxy-3-methacryl 
oyloxypropan-1-yl carbamate, 
N-(3-isopropenyl-.alpha.,.alpha.dimethylbenzyl)-2,3-dimethacryloyloxy-1-yl 
carbamate, 
N-(4-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)-2,3-diacryloyloxypropan-1 
-yl carbamate, 
N-(4-isopropenyl-.alpha.,.alpha.-dimethylbenzyl.alpha.,.alpha.)-2-acryloyl 
oxy-3-methacryloyloxypropan-1-yl carbamate, 
N-(4-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)-2,3-dimethacryloyloxy-1-y 
l carbamate, 
N-(3-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)-2,2-diacryloyloxymethyl-3 
-acryloyloxypropyl carbamate 
N-.alpha.,.alpha.(3-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)-2,2-dimeth 
acryloyloxymethyl3-methacryloyloxydipropyl carbamate, 
N-(4-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)-2,2-diacryloyloxymethyl-3 
-acryloyloxypropyl carbamate, and 
N-(4-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)-2,2-dimethacryloyloxymeth 
yl-3-methacryloyloxypropyl carbamate. 
These compounds can be produced by conducting a urethanization reaction of 
3-isopropenyl-.alpha.,.alpha.-dimethylbenzyl isocyanate or 
4-isopropenyl-.alpha.,.alpha.-dimethylbenzyl isocyanate with glycerol 
diacrylate, glycerol acrylate methacrylate, glycerol dimethacrylate, 
pentaerythritol triacrylate or pentaerythritol trimethacrylate, 
pentaerythritol acrylate dimethacrylate, pentaerythritol methacrylate 
diacrylate. Optionally, a solvent for the reagents may be or may not be 
used and optionally the reaction is effected in the presence of a 
urethanization-promoting catalyst. 
The above reaction is carried out such that from about 1 to about 1.2 mol, 
preferably from about 1 to about 1.5 mol, of glycerol diacrylate, glycerol 
acrylate methacrylate, glycerol dimethacrylate, pentaerythritol 
triacrylate or pentaerythritol trimethacrylate is added to about 1 mol of 
3-isopropenyl-.alpha.,.alpha.-dimethylbenzyl isocyanate or 
4-isopropenyl-.alpha.,.alpha.-dimethylbenzyl isocyanate. Preferably, the 
reaction is carried out in a solvent that will not react with the 
reagents, such as hexane, benzene, and toluene. The temperature of the 
reaction medium is kept at from about 25 to about 110 .degree. C., 
preferably from about 40 to about 65 .degree. C., and optionally a 
urethanization-promoting catalyst such as dibutyl tin dilaurate is added 
in an amount of 0.1 to 5 wt. %, preferably 0.5 to 3 wt. %, based on the 
weight of the isocyanate. 
After the reaction is complete, the reaction medium is purified by 
chromatography to yield a polyfunctional carbamic ester monomer according 
to the present invention. 
The third group of the present novel polyfunctional monomers comprises a 
difunctional monomer represented by the general formula (VI): 
##STR8## 
wherein R.sub.10 represents hydrogen or a methyl group. 
Specific and non-limiting examples thereof include 
N-(3-isopropenyl-.alpha.,.alpha.-dimethylbenzyl.alpha.,.alpha.)-5-acryloyl 
oxymethylene-N-(4-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)-5-acryloyloxy 
methylene-2-oxazolidone, 
N-(3-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)-5-methacryloyloxymethylen 
e-2-oxazolidone, and 
N-(4-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)-5-methacryloyloxymethylen 
e-2-oxazolidone 
These compounds are produced by adding from about 0.8 to about 1.20 mol, 
preferably from about 0.95 to 1.05 mol of glycidyl acrylate or glycidyl 
methacrylate dropwise to 1 mol of 
3-isopropenyl-.alpha.,.alpha.-dimethylbenzyl isocyanate 
4-isopropenyl-.alpha.,.alpha.-dimethylbenzyl isocyanate in a solvent that 
will not react with the reagents such as benzene, toluene or xylene. The 
reaction is carried out in the presence of an oxazolidone-producing 
reaction catalyst such as tributylphosphine oxide-lithium bromide, in an 
amount of from about 1.0 to about 10 mol %, preferably from about 1.5 to 
about 5.0 mol %, relative to the 
3-isopropenyl-.alpha.,.alpha.dimethylbenzyl isocyanate or 
4-isopropenyl-.alpha.,.alpha.dimethylbenzyl isocyanate. The temperature of 
the reaction medium is kept at from about 70.degree. to about 150.degree. 
C., preferably from about 90 to about 120 .degree. C., so as to allow the 
reaction to proceed. After the reaction is complete, the reaction medium 
is purified by chromatography to yield a difunctional monomer having the 
general formula (VI). 
Since the present novel polyfunctional monomer has both a functional group 
whose polymerization speed is high and an isopropenyl group whose 
polymerization speed is low, where functional group and isopropenyl group 
will be homopolymerized or copolymerized with a monomer having an acryl 
group, a methacryl group, a vinylphenyl group, or the like, the control of 
polymerization is quite easy and a resin can be obtained that is highly 
transparent and at the same time has excellent surface hardness, heat 
resistance, and workability as regards severing and cutting thereof, in 
comparison to polymethyl methacrylate, polystyrene, polycarbonate, and 
polydiethylene glycol bisallyl carbonate. Selection of the polymerization 
conditions of the present monomer is easy. The present polyfunctional 
monomers are useful as starting materials for producing resins that are 
suitable for use as glazing materials, for example, for parts pertaining 
to vehicle's components such as car windows, and for optical elements such 
as optical disk substrates and lenses of spectacles and cameras. 
EXAMPLES 
The present invention will now be described more particularly with 
reference to the following Examples, but of course the present invention 
is not limited by the Examples. Other examples within the scope of the 
invention will be readily apparent to those skilled in the art from a 
reading of the present disclosure and from practicing the invention. 
In the Examples, the parts quoted are parts by weight.

EXAMPLE 1 
8.3 parts of 3-isopropenyl-.alpha.,.alpha.-dimethylbenzyl isocyanate, 10.0 
parts of toluene, and 4.8 parts of 2-hydroxyethyl acrylate were mixed, and 
the resulting reaction was carried out for 5 hours with stirring while the 
temperature of the reaction medium was kept at 100 .degree. C. After the 
reaction was complete, the reaction medium was condensed. The condensed 
medium was purified by chromatography to yield 2.9 parts of 
N-(3-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)-2-acryloyloxyethyl 
carbamate that was colorless and syrupy. 
Elemental analysis figures (calculated for C.sub.18 H.sub.23 NO.sub.4): 
______________________________________ 
C H N 
______________________________________ 
Found (%) 67.62 7.29 4.39 
Calculated (%) 
68.12 7.31 4.42 
______________________________________ 
##STR9## 
EXAMPLE 2 
10.0 parts of 3-isopropenyl-.alpha.,.alpha.-dimethylbenzyl isocyanate, 6.5 
parts of 2-hydroxyethyl methacrylate, and 0.1 part of dibutyl tin 
dilaurate (used as a urethanization reaction-promoting catalyst) were 
mixed, and the resulting reaction was carried out for 1 hour with stirring 
while the temperature of the reaction medium was kept at 65.degree. C. 
After the reaction was complete, the reaction medium was purified by 
chromatography to yield 14.0 parts of 
N-(3-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)-2-methacryloyloxyethyl 
carbamate that was colorless and syrupy. 
Elemental analysis figures (calculated for C.sub.19 H.sub.25 NO.sub.4 ): 
______________________________________ 
C H N 
______________________________________ 
Found (%) 68.77 7.32 4.28 
Calculated (%) 
68.86 7.61 4.23 
______________________________________ 
##STR10## 
EXAMPLE 3 
The procedure of Example 1 was repeated except that 8.3 parts of 4- 
isopropenyl-.alpha.,.alpha.-dimethylbenzyl isocyanate were used instead of 
8.3 parts of 3-isopropenyl-.alpha.,.alpha.-dimethylbenzyl isocyanate, 
thereby producing 3.2 parts of 
N-(4-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)-2-acryloyloxyethyl 
carbamate that was colorless and syrupy. 
Elemental analysis figures (calculated for C.sub.18 H.sub.23 NO.sub.4 ) 
______________________________________ 
C H N 
______________________________________ 
Found (%) 67.90 7.27 4.37 
Calculated (%) 
68.12 7.31 4.42 
______________________________________ 
##STR11## 
EXAMPLE 4 
The procedure of Example 2 was repeated except that 10.0 parts of 
4-isopropenyl-.alpha.,.alpha.-dimethylbenzyl isocyanate were used instead 
of 10.0 parts of 3-isopropenyl-.alpha.,.alpha.dimethylbenzyl isocyanate, 
thereby producing 14.2 parts of 
N-(4-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)-2-methacryloyloxyethyl 
carbamate that was colorless and syrupy. 
Elemental analysis figures (calculated for C.sub.19 H.sub.25 NO.sub.4): 
______________________________________ 
C H N 
______________________________________ 
Found (%) 68.53 7.40 4.19 
Calculated (%) 
68.86 7.61 4.23 
______________________________________ 
##STR12## 
EXAMPLE 5 
The procedure of Example 2 was repeated, except that 6.5 parts of 
2-hydroxypropyl acrylate were used instead of 6.5 parts of 2- hydroxyethyl 
methacrylate, and the temperature of the reaction medium was maintained at 
80.degree. C. instead of 65.degree. C., thereby producing 13.8 parts of 
N-(3-isopropenyl-.alpha.-dimethylbenzyl)-1-acryloyloxypropan-2-yl 
carbamate that was colorless and syrupy. 
Elemental analysis figures (calculated for C.sub.19 H.sub.25 NO.sub.4): 
______________________________________ 
C H N 
______________________________________ 
Found (%) 68.66 7.53 4.29 
Calculated (%) 
68.86 7.61 4.23 
______________________________________ 
##STR13## 
EXAMPLE 6 
The procedure of Example 2 was repeated, except that 7.5 parts of 2- 
hydroxypropyl methacrylate were used instead of 6.5 parts of 
2-hydroxyethyl methacrylate, the temperature of the reaction medium was 
maintained at 80.degree. C. instead of 65.degree. C., and the amount of 
the dibutyl tin laurate used was 0.2 part instead of 0.1 part, thereby 
producing 15.1 parts of N-(3-isopropenyl-.alpha.,.alpha.- 
dimethylbenzyl.alpha.,.alpha.}-1-methacryloyloxypropan-2-yl carbamate that 
was colorless and syrupy. 
Elemental analysis figures (calculated for C.sub.20 H.sub.27 NO.sub.4): 
______________________________________ 
C H N 
______________________________________ 
Found (%) 69.45 7.71 4.01 
Calculated (%) 
69.54 7.87 4.05 
______________________________________ 
##STR14## 
EXAMPLE 7 
10.0 parts of 4-isopropenyl-.alpha.,.alpha.-dimethylbenzyl isocyanate, 6.7 
parts of 2-hydroxypropyl acrylate, 10.0 parts of benzene, and 0.5 part of 
dibutyl tin dilaurate (used as a reaction-promoting catalyst) were mixed, 
and the resulting reaction was carried out for 5 hours with stirring while 
the temperature of the reaction medium was kept at 60.degree. C. After the 
reaction was complete, the reaction medium was purified by chromatography 
to yield 12.8 parts of 
N-(4-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)-1-acryloyloxypropan-2-car 
bamate that was colorless and syrupy. 
Elemental analysis figures (calculated for C.sub.19 H.sub.25 NO.sub.4 
.alpha.,.alpha.) 
______________________________________ 
C H N 
______________________________________ 
Found (%) 68.45 7.44 4.07 
Calculated (%) 
68.86 7.61 4.23 
______________________________________ 
##STR15## 
EXAMPLE 8 
12.0 parts of 3-isopropenyl-.alpha.,.alpha.-dimethylbenzyl isocyanate, 10.0 
parts of toluene, and 11.9 parts of glycerol-1,3-diacrylate were mixed, 
and the resulting reaction was carried out for 3 hours with stirring while 
the temperature of the reaction medium was kept at 90.degree. C. After the 
the reaction was complete, the reaction medium was condensed. The 
condensed medium was purified by chromatography to yield 2.4 parts of 
N-(3-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)-1,3-diacryloyloxypropan-2 
-yl carbamate that was colorless and syrupy. 
Elemental analysis figures (calculated for C.sub.22 H.sub.27 NO.sub.6): 
______________________________________ 
C H N 
______________________________________ 
Found (%) 65.54 6.57 3.33 
Calculated (%) 
65.82 6.78 3.49 
______________________________________ 
##STR16## 
EXAMPLE 9 
48.0 parts of 3-isopropenyl-.alpha.,.alpha.-dimethylbenzyl isocyanate, 54.4 
parts of glycerol-1,3-dimethacrylate, and 0.5 part of dibutyl tin 
dilaurate (used as a reaction promoting catalyst) were mixed, and the 
resulting reaction was carried out for 1 hour with stirring while the 
temperature of the reaction medium was kept at 60 .degree. C. After the 
reaction was complete, the reaction medium was purified by chromatography 
to yield 63.0 parts of N-(3-isopropenyl-.alpha., 
.alpha.-dimethylbenzyl-1,3-dimethacryloyloxypropan-2-yl carbamate that was 
colorless and syrupy. Elemental analysis figures (calculated for C.sub.24 
H.sub.31 N06) 
______________________________________ 
C H N 
______________________________________ 
Found (%) 66.90 7.13 3.09 
Calculated (%) 
67.11 7.27 3.26 
______________________________________ 
##STR17## 
EXAMPLE 10 
The procedure of Example 9 was repeated, except that 51.5 parts of 
glycerol-1-acrylate-3-methacrylate were used instead of 54.4 parts of 
glycerol-1,3-dimethacrylate, thereby producing 71.0 parts of 
N-(3-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)-1-acryloyloxy-3-methacryl 
oyloxypropan-2-yl carbamate that was colorless and syrupy. 
Elemental analysis figures (calculated for C.sub.23 H.sub.29 NO.sub.6): 
______________________________________ 
C H N 
______________________________________ 
Found (%) 66.11 6.99 3.23 
Calculated (%) 
66.49 7.04 3.37 
______________________________________ 
##STR18## 
EXAMPLE 11 
The procedure of Example 9 was repeated, except that 48.0 of parts of 4- 
isopropenyl-.alpha.,.alpha.-dimethylbenzyl isocyanate, and 47.8 parts of 
glycerol-1 3-diacrylate were used instead of 48.0 parts of 
3-isopropenyl-.alpha.,.alpha.-dimethylbenzyl isocyanate, and 54.4 parts of 
glycerol-1 3dimethacrylate, respectively, thereby producing 62.1 parts of 
N-(4-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)-1 
3-diacryloyloxypropan-2-yl carbamate that was colorless and syrupy. 
Elemental analysis figures (calculated for C.sub.22 H.sub.27 NO.sub.6): 
______________________________________ 
C H N 
______________________________________ 
Found (%) 65.31 6.49 3.40 
Calculated (%) 
65.82 6.78 3.49 
______________________________________ 
##STR19## 
EXAMPLE 12 
The procedure of Example 9 was repeated, except that 71.2 parts of 
pentaerythritol triacrylate were used instead of 54.4 parts of 
glycerol-1,3-dimethacrylate, thereby producing 50.2 parts of 
N-(3-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)-2,2-diacryloyloxymethyl-3 
-acryloyloxypropyl carbamate that was colorless and syrupy. 
Elemental analysis figures (calculated for C.sub.27 H.sub.33 NO.sub.8): 
______________________________________ 
C H N 
______________________________________ 
Found (%) 64.19 6.37 2.80 
Calculated (%) 
64.92 6.66 2.80 
______________________________________ 
##STR20## 
EXAMPLE 13 
The procedure of Example 9 was repeated, except that 48.0 parts of 
4-isopropyl-.alpha.,.alpha.dimethylbenzyl isocyanate, and 81.3 parts of 
pentaerythritol trimethacrylate were used instead of 48.0 parts of 
3-isopropenyl-.alpha.,60 -dimethylbenzyl isocyanate, and 54.4 parts of 
glycerol-1,3-dimethacrylate, respectively, thereby producing 77.1 parts of 
N-(4-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)-2,2-dimethacryloyloxymeth 
yl-3-methacryloyloxypropyl carbamate that was colorless and syrupy. 
Elemental analysis figures (calculated for C.sub.30 H.sub.39 NO.sub.8) 
______________________________________ 
C H N 
______________________________________ 
Found (%) 66.11 7.00 2.50 
Calculated (%) 
66.53 7.26 2.59 
______________________________________ 
##STR21## 
EXAMPLE 14 
The procedure of Example 8 was repeated, except that 11.9 parts of 
glycerol-2,3-diacrylate were used instead of 11.9 parts of 
glycerol-1,3-diacrylate, thereby producing 2.8 parts of 
N-(3-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)-2,3-diacryloyloxypropan-1 
-yl carbamate that was colorless syrupy. 
Elemental analysis figures (calculated for C.sub.22 H.sub.27 NO.sub.6): 
______________________________________ 
C H N 
______________________________________ 
Found (%) 65.69 6.46 3.31 
Calculated (%) 
65.82 6.78 3.49 
______________________________________ 
##STR22## 
EXAMPLE 15 
20.0 parts of 3-isopropenyl-.alpha.,.alpha.-dimethylbenzyl isocyanate, 50.0 
parts of toluene, 0.8 part of tributylphosphine oxide, and 0.2 part of 
lithium bromide were refluxed with stirring, and 12.9 parts of glycidyl 
acrylate were added dropwise thereto under reflux and the resulting 
reaction was allowed to proceed for 1 hour. After the reaction was 
complete, the reaction medium was condensed and purified by 
chromatography, thereby yielding 24.2 parts of 
N-(3-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)-5-acryloyloxymethylene-2- 
oxazolidone that was colorless and watery. 
Elemental analysis figures (calculated for C.sub.19 H.sub.23 NO.sub.4 ): 
______________________________________ 
C H N 
______________________________________ 
Found (%) 68.92 6.91 4.37 
Calculated (%) 
69.28 7.04 4.25 
______________________________________ 
##STR23## 
EXAMPLE 16 
The procedure of Example 15 was repeated, except that 20.2 parts of 
4-isopropenyl-.alpha.,.alpha.-dimethylbenzyl isocyanate were used instead 
of 20.2 parts of 3-isopropenyl-.alpha.,.alpha.dimethylbenzyl isocyanate, 
thereby producing 25.5 parts of 
N-(4-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)-5-acryloyloxymethylene-ox 
azolidone 2-oxazolidone that was colorless and watery. 
Elemental analysis figures (calculated for C.sub.19 H.sub.23 NO.sub.4 ) 
______________________________________ 
C H N 
______________________________________ 
Found (%) 69.56 7.18 4.21 
Calculated (%) 
69.28 7.04 4.25 
______________________________________ 
##STR24## 
EXAMPLE 17 
20.7 parts of 3-isopropenyl-.alpha.,.alpha.-dimethylbenzyl isocyanate, 50.0 
parts of toluene, 0.8 parts of tributylphosphine oxide, and 0.2 part of 
lithium bromide were stirred under reflux, 14.2 parts of glycidyl 
methacrylate were added thereto dropwise, and the resulting reaction was 
allowed to proceed under reflux for 1 hour. After the reaction was 
complete, the reaction medium was condensed, and then was purified by 
chromatography to yield 30.6 parts of 
N-(3-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)-5-methacryloyloxymethylen 
e-2-oxazolidone that was colorless and watery. 
Elemental analysis figures (calculated for C.sub.20 H.sub.25 NO.sub.4): 
______________________________________ 
C H N 
______________________________________ 
Found (%) 70.16 7.05 4.23 
Calculated (%) 
69.95 7.34 4.08 
______________________________________ 
##STR25## 
EXAMPLE 18 
The procedure of Example 17 was repeated, except that 20.2 parts of 
4-isopropenyl-.alpha.,.alpha.-dimethylbenzyl isocyanate were used instead 
of 20.02 parts of 3-isopropenyl-.alpha.,.alpha.dimethylbenzyl isocyanate, 
thereby producing 28.6 parts of 
N-(4-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)-5-methacryloyloxymethylen 
e-2-oxazolidone that was colorless and watery. 
Elemental analysis figures (calculated for C.sub.20 H.sub.25 NO.sub.4 ): 
______________________________________ 
C H N 
______________________________________ 
Found (%) 69.71 7.16 4.17 
Calculated (%) 
69.95 7.34 4.08 
______________________________________ 
##STR26## 
APPLICATION EXAMPLES 
Various applications of the present invention will now be described with 
reference to Application Examples, wherein the parts quoted represent 
parts by weight and the percentages quoted represent percent by weight. 
Application Example 1 
30.0 parts of 
N-(3-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)-2-methacryloyloxyethyl 
carbamate, 0.1 part of bis(4-t-butylcyclohexyl) peroxydicarbonate, and 0.1 
part of t-butyl peroxyisopropyl carbonate were mixed to form a uniform 
mixture, and the mixture was deaerated under reduced pressure and cast in 
a mold composed of a 150 mm.times.150 mm glass sheet, and a vinyl chloride 
gasket The cast mixture was then polymerized for 1 hour at 60.degree. C., 
and further for 1 hour at 120.degree. C., whereafter the platelike 
polymerized item was removed from the mold. The hardness of the plate, as 
measured by the pencil hardness method 
.alpha.,.alpha.(JIS-K-5401.alpha.,.alpha.), was found to be 5H, the 
chemical resistance thereof was good, severing of the plate with a metal 
severing saw was possible, and grinding of the plate with a lens polisher 
for machining lenses of spectacles was also possible. The results of these 
tests, together with the results obtained in Application Examples 2 to 6, 
are given in Table 1. 
The physical properties were measured by the following methods: 
(1) Appearance: the platelike polymerized item was visually observed, 
without magnification. 
(2) Light transmittance: was measured in accordance with ASTM D1003. 
(3) Surface hardness: a pencil hardness test for paints according to JIS 
K-5401 was used. 
(4) Heat resistance: after the polymerized item was allowed to stand in a 
hot-air drying chamber at 120.degree. C. for 1 hour, it was visually 
observed, without magnification. When it was not colored and was free from 
surface imperfections, it was judged to be O and when it was colored and 
had surface imperfections, it was judged to be X. 
(5) Workability when the polymerized item could be ground by a machine for 
working lenses of spectacles, it was judged to be O), and when it could 
not be cut, it was judged to be X. 
(6) Chemical resistance: the polymerized item was immersed in isopropanol 
and toluene at room temperature for 24 hours. When it was not marked by an 
HB pencil, it was judged as O, whereas when it was marked by an HB pencil, 
it was judged as X. 
Application Example 2 
The procedure of Application Example 1 was repeated, except that 30.0 parts 
of 
N-(3-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)-1-acryloyloxypropan-2-yl 
carbamate were used instead of 30.0 parts of 
N-(3-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)-2-methacryloyloxyethyl 
carbamate, thereby producing a platelike polymerized item. 
The pencil hardness of the plate was 5H, the chemical resistance thereof 
was good, severing of the plate with a metal cutting saw was possible, and 
grinding of the plate with a lens polisher for working lenses of 
spectacles was also possible. 
Application Example 3 
The procedure of Application Example 1 was repeated except that 30.0 parts 
of N-(4-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)-2-acryloyl-oxyethyl 
carbamate were used instead of 30.0 parts of 
N-(3-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)-2-methacryloyloxyethyl 
carbamate, thereby producing a platelike polymerized item. 
The pencil hardness of the plate was 5H, the chemical resistance thereof 
was good, severing of the plate with a metal cutting saw was possible, and 
grinding of the plate with a lens polisher for working lenses of 
spectacles was also possible. 
Application Example 4 
The procedure of Application Example 1 was repeated, except that 30.0 parts 
of 
N-(4-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)-1-methacryloyloxypropan-2 
-yl carbamate were used instead of 30.0 parts of 
N-(3-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)-2-methacryloyloxyethyl 
carbamate, thereby producing a platelike polymerized item. 
The pencil hardness of the plate was 5H, the chemical resistance thereof 
was good, severing of the plate with a metal cutting saw was possible, and 
grinding of the plate with a lens polisher for working lenses of 
spectacles was also possible. 
Application Example 5 
30.0 parts of 
N-(3-isopropenyl-.alpha.,.alpha.dimethylbenzyl)acryloyloxyethyl carbamate, 
1.5 parts of styrene, 0.1 part of t-butyl peroxypivalate, and 0.1 part of 
t-butyl peroxyisopropyl carbonate were mixed uniformly, and the resulting 
mixture was cast in a mold composed of a 150 mm.times.150 mm glass sheet, 
and a vinyl chloride gasket. After polymerization at 70 .degree. C. for 1 
hour, and further at 120.degree. C. for 1 hour, a platelike polymerized 
item was removed from the mold. 
The pencil hardness of the plate was 5H, the chemical resistance thereof 
was good, severing of the plate with a metal cutting saw was possible, and 
grinding of the plate with a lens polisher for working lenses of 
spectacles was also possible. 
Application Example 6 
30.0 parts of 
N-(4-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)methacryloyloxypropyl 
carbamate, 1.5 parts of methyl methacrylate, 0.1 part of 
bis(4-t-butylcyclohexyl) peroxydicarbonate, and 0.1 part of t-butyl 
peroxyisopropyl carbonate were mixed uniformly, and the resulting mixture 
was cast in a mold composed of a 150 mm.times.150 mm glass sheet, and a 
vinyl chloride gasket. After polymerization at 60.degree. C. for 1 hour, 
and further at 120.degree. C. for 1 hour, a platelike polymerized item was 
removed from the mold. 
The pencil hardness of the plate was 5H, chemical resistance thereof was 
good, severing of the plate with a metal cutting saw was possible, and 
grinding of the plate with a lens polisher for working lenses of 
spectacles was also possible. 
TABLE 1 
__________________________________________________________________________ 
Application 
Application 
Application 
Application 
Application 
Application 
Example 1 
Example 2 
Example 3 
Example 4 
Example 5 
Example 6 
__________________________________________________________________________ 
Appearance 
colorless, 
colorless 
colorless 
colorless 
colorless 
colorless 
transparent 
transparent 
transparent 
transparent 
transparent 
transparent 
Light 91 91 91 90 90 91 
transmittance (%) 
Surface hardness 
5H 5H 5H 5H 5H 5H 
Heat resistance 
O O O O O O 
Workability 
O O O O O O 
Chemical resistance 
O O O O O O 
__________________________________________________________________________ 
Application Example 7 
30.0 parts of 
N-(3-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)-1,3-diacryloyloxypropan-2 
-yl carbamate, 0.03 part of lauroyl peroxide, and 0.15 part of benzoyl 
peroxide were mixed uniformly, and the resulting mixture was cast in a 
mold composed of a 150 mm.times.150 mm glass sheet, and a vinyl chloride 
gasket. After polymerization at 55 .degree. C. for 1 hour, and further at 
130.degree. C. for 1 hour, a platelike polymerized item was removed from 
the mold. The physical properties thereof are shown in Table 2 together 
with those of Application Examples 8 to 11. 
Application Example 8 
The procedure of Application Example 7 was repeated, except that 30.0 parts 
of 
N-(3-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)-1,3-dimethacryloyloxyprop 
an-2-yl carbamate were used instead of 30.0 parts of 
N-(3-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)-1,3-diacryloyloxypropan-2 
-yl carbamate, the polymerization was effected for 1 hour at 60.degree. C. 
instead of 55.degree. C., and further for 2 hours at 140.degree. C. 
instead of 130.degree. C., thereby producing a platelike polymerized item. 
Application Example 9 
The procedure of Application Example 8 was repeated except that 30.0 parts 
of 
N-(3-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)-1-acryloyloxy-3-methacryl 
oyloxypropan-2-yl carbamate were used instead of 30.0 parts of 
N-(3-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)-1,3-dimethacryloyloxyprop 
an2-yl carbamate, thereby producing a platelike polymerized item. 
Application Example 10 
The procedure of Application Example 8 was repeated except that 30.0 parts 
of 
N-(4-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)-1,3-acryloyloxypropan-2-y 
l carbamate were used instead of 30.0 parts of 
N-(3-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)-1,3-dimethacryloyloxyprop 
an-2-yl carbamate, thereby producing a platelike polymerized item. 
Application Example 11 
30.0 parts of 
N-(3-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)-2,2-diacryloyloxymethyl-3 
-acryloyloxypropyl carbamate, 0.01 part of lauroyl peroxide, and 0.15 part 
of t-butyl peroxy-2-ethyl hexanoate were mixed uniformly, and the 
resulting mixture was cast in a mold composed of a 150 mm.times.150 mm 
glass sheet, and a vinyl chloride gasket. After polymerization at 55 
.degree. C. for 1 hour, and further at 130.degree. C. for 2 hours, a 
platelike polymerized item was removed from the mold. 
TABLE 2 
__________________________________________________________________________ 
Application 
Application 
Application 
Application 
Application 
Example 7 
Example 8 
Example 9 
Example 10 
Example 11 
__________________________________________________________________________ 
Appearance 
colorless, 
colorless 
colorless 
colorless 
colorless 
transparent 
transparent 
transparent 
transparent 
transparent 
Light 91 91 91 91 91 
transmittance (%) 
Surface hardness 
9H 5H 6H 9H 9H 
Heat resistance 
O O O O O 
Workability 
O O O O O 
Chemical resistance 
O O O O O 
__________________________________________________________________________ 
Application Example 12 
0.2 part of benzoyl peroxide was added to 20.0 parts of 
N-(3-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)-5-acryloyloxymethylene-2- 
oxazolidone, they were mixed well, and the mixture deaerated to form a 
uniform liquid. The liquid was then cast in a mold composed of a 150 
mm.times.150 mm glass sheet, and a vinyl chloride gasket. After 
polymerization at from 55.degree. C. to 140.degree. C. for 1.5 hours in a 
hot-air oven for polymerization, a platelike polymerized item was removed 
from the mold. The physical properties are shown in Table 3 together with 
those of Application Examples 13 to 15. 
Application Example 13 
The procedure of Application Example 12 was repeated, except that 20.0 
parts of N-(4-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)-5- 
acryloyloxymethylene-2-oxazolidone were used instead of 20.0 parts of 
N-(3-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)-5-acryloyloxymethylene-2- 
oxazolidone, thereby producing a platelike polymerized item. 
Application Example 14 
The procedure of Application Example 12 was repeated, except that 20.0 
parts of 
N-(3-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)-5-methacryloyloxymethylen 
e-2-oxazolidone were used instead of 20.0 parts of 
N-(3-isopropenyldimethylbenzyl)-5-acryloyloxymethylene-2-oxazolidone, 
thereby producing a platelike polymerized item. 
Application Example 15 
The procedure of Application Example 12 was repeated except that 20.0 parts 
of 
N-(4-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)-5-methacryloyloxymethylen 
e-2-oxazolidone were used instead of 20.0 parts of 
N-(3-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)-5-acryloyloxymethylene-2- 
oxazolidone, thereby producing a platelike polymerized item. 
Although the present invention has been described in connection with 
various preferred embodiments thereof, it is evident that other 
embodiments thereof will be apparent to those skilled in the art from a 
reading of the present specification and practice of the invention 
disclosed herein. Accordingly, it is intended that the true scope and 
spirit of the invention be indicated by the following claims. 
TABLE 3 
______________________________________ 
Application 
Application 
Application 
Application 
Example 12 
Example 13 
Example 14 
Example 15 
______________________________________ 
Appearance 
O O O O 
Surface 5H 5H 4H 4H 
hardness 
Heat O O O O 
resistance 
Chemical O O O O 
resistance 
Workability 
O O O O 
______________________________________