Polymerizable monomer having at least one isopropenyl phenyl group and being capable of forming a high surface hardness transparent resin

The present invention relates to a high surface hardness transparent resin having excellent scratch resistance, heat resistance and chemical resistance, a glazing material, a protective cover for display devices, an optical lens and a hard coat material comprising the aforesaid resin, and a novel polymerizable monomer which is useful as a raw material of the above-mentioned resin. The monomer is represented by the formula (I) ##STR1## (wherein R is an aliphatic residue having or not having an halogen atom, an oxygen atom, an alicyclic ring, a heterocyclic ring or an aromatic ring, an alicyclic residue, or a heterocyclic residue, n is an integer of 1 to 4, when n=1, X is oxygen or sulfur, when n.gtoreq.2, X's are all oxygen or all sulfur, one X is oxygen while the other X or X's are sulfur, one X is sulfur while the other X or X's are oxygen, or two X's are oxygen while the other X's are sulfur). The aforesaid high surface hardness transparent resin comprises a crosslinked polymer prepared by copolymerizing a monomer (A) represented by the formula (I) and a monomer (B) having, in one molecule, m functional groups of at least one kind selected from the group consisting of CH.sub.2 .dbd.CH--C(O)--O--, CH.sub.2 .dbd.C(CH.sub.3)--C(O)--O-- and ##STR2## where (n+m) is an integer of 3 or more.

BACKGROUND OF THE INVENTION 
(i) Field of the Invention 
The present invention relates to a transparent resin which has high surface 
hardness and exhibits excellent scratch resistance, heat resistance and 
chemical resistance. The invention also relates to a glazing material, a 
protective cover for display devices, an optical lens and a hard coat 
material comprising the resin and a novel polymerizable monomer useful as 
a raw material for the high surface hardness transparent resin. 
(ii) Description of the Prior Art 
Methacrylic resin, polycarbonate resin and polystyrene resin exhibit 
excellent transparency, impact resistance, workability and mass 
productivity, and therefore have been used as a glazing material such as 
for windowpanes in vehicles, houses, schools and sports facilities, 
baseboards of verandas, and balconies, protective covers for display 
devices such as various dashboards, displays for computers, liquid crystal 
televisions and front boards of vending machines, optical lenses, 
illuminator covers, signboards, protective glasses, optical photodisc 
substrates and the like. Particularly, when the above-mentioned resins are 
applied as glazing materials, protective covers for display devices and as 
optical lenses, it is necessary that such resins have high scratch 
resistance, i.e., high surface hardness, chemical resistance, heat 
resistance and the like to achieve good visibility and desired appearance 
transparency, optical physical properties, mechanical strength stiffness 
and the like. 
However, the above-mentioned transparent resins are linear polymers, and 
therefore do not exhibit the requisite surface hardness, chemical 
resistance and heat resistance. In addition, even if these resins are 
coated with a hard coat to improve their surface hardness and chemical 
resistance, sufficient performance cannot always be obtained. 
For the purpose of solving these problems, a transparent resin has been 
proposed which comprises a polymer having a crosslinking structure such as 
diethylene glycol diallylcarbonate resin or a urethane polyacrylate 
(Japanese Patent Laid-open Publication Nos. 3610/1986 and 75022/1988). 
However, the proposed resins are prepared by the mutual polymerization of 
an allyl group, an acrylic group or a methacylic group, polymerization 
rates of which are on a similar and therefore problems exist such as 
difficulty of controlling the rate of polymerization run-away reactions 
and a long period of time is required to obtain a polymer having a good 
surface state and a low polymerization strain. 
SUMMARY OF THE INVENTION 
The present invention overcomes the problems and disadvantages of the prior 
art by providing a high surface hardness transparent resin prepared by 
combining an isopropenylphenyl group having a low polymerization rate with 
another polymerizable group having a high polymerization rate, i.e. by 
copolymerizing a compound having at least one isopropenylphenyl groups in 
one molecule thereof and another compound having an acryloyl group, a 
methacryloyl group or a vinylphenyl group in which the radical 
polymerizability is higher than in the isopropenylphenyl group. 
An object of the present invention is to provide a transparent resin which 
can be prepared by an easily controlled polymerization reaction and which 
has a high surface hardness and exhibits excellent chemical resistance and 
heat resistance. 
Another object of the present invention is to provide a monomer having a 
polymerizable group which has a polymerization rate slower than an acrylic 
group, a methacrylic group and a vinylphenyl group and which exhibits 
excellent copolymerizability with these groups, and which can be formed 
into a polymer having a high surface hardness and excellent transparency, 
heat resistance and chemical resistance properties. 
Additional objects and advantages of the invention will be set forth in 
part in the description which follows, and in part will be obvious from 
the description, or may be learned by practice of the invention. The 
objects and advantages of the invention will be realized and attained by 
means of the instrumentalities and combinations, particularly pointed out 
in the appended claims. 
To achieve the objects and in accordance with the purpose of the invention, 
as embodied and broadly described herein, in a first embodiment, the 
present invention provides a high surface hardness transparent resin 
comprising a crosslinked polymer prepared by copolymerizing a monomer (A) 
represented by the formula (I) 
##STR3## 
(wherein R is an aliphatic residue having or not having a halogen atom, an 
oxygen atom, an alicyclic ring, a heterocyclic ring or an aromatic ring, 
an alicyclic residue, or a heterocyclic residue, n :s an integer of 1 to 
4, when n=1, X is oxygen or sulfur, when n.gtoreq.2, X's are all oxygen or 
all sulfur, one X is oxygen while the other X or X's are sulfur, one X is 
sulfur while the other X or X's are oxygen, or two X's are oxygen while 
the other X's are sulfur) and a monomer (B) having, in one molecule, m 
functional groups of at least one kind selected from the group consisting 
of CH.sub.2 .dbd.CH--C(O)--O--, CH.sub.2 .dbd.C(CH.sub.3)--C(O)--O--and 
##STR4## 
where (n+m) is an integer of 3 or more. 
In a second embodiment, the present invention provides a high surface 
hardness transparent resin comprising a crosslinked polymer containing a 
structural unit represented by the following formula (II) and/or (III) 
comprising the monomer (A) and the monomer (B) set forth above: 
##STR5## 
(wherein X is oxygen or sulfur, R is an aliphatic residue having or not 
having a halogen atom, an oxygen atom, an alicyclic ring, a heterocyclic 
ring or an aromatic ring, an alicyclic residue, or a heterocyclic residue, 
R' is hydrogen or methyl, Y is, similar or dissimilar, 
##STR6## 
n is an integer of 1-4, and ( n+m ) is an integer of 3 or more). 
In a third embodiment, the present invention provides a glazing material 
comprising a high surface hardness transparent resin described in the 
first embodiment of the invention. 
In a fourth embodiment the present invention provides a protective cover 
for display devices comprising the high surface hardness transparent resin 
described in the first embodiment of the invention. 
In a fifth embodiment the present invention provides an optical lens 
comprising the high surface hardness transparent resin described in the 
first embodiment of the invention. 
In sixth embodiment the present invention provides a hard coat material 
comprising the high surface hardness transparent resin described in the 
first embodiment of the present invention. 
In a seventh embodiment of the present invention provides a high surface 
hardness transparent resin comprising a crosslinked polymer prepared by 
copolymerizing a monomer (A) of at least one kind selected from the group 
consisting of monomers represented by the formulae (IV), (V) and (VI): 
##STR7## 
wherein when n is 1, R is selected from the group consisting of 
--CH.sub.3, --C.sub.2 H.sub.5, --C.sub.3 H.sub.7, --C.sub.4 H.sub.9, 
--C.sub.5 H.sub.11, --C.sub.6 H.sub.13, --CH.sub.2 CCl.sub.3, --CH.sub.2 
CF.sub.3, 
##STR8## 
and the substituent on the aromatic ring is present at the m-position or 
the p-position thereof, 
##STR9## 
wherein when n is 2, R is selected from the group consisting of 
##STR10## 
and the substituent on the aromatic ring is present at the m-position or 
the p-position thereof, 
##STR11## 
wherein when n is 3, R is selected from the group consisting of 
##STR12## 
and the substituent on the aromatic ring is present at the m-position or 
the p-position thereof and a monomer (B) having, in one molecule, m 
functional groups of at least one kind selected from the group consisting 
of CH.sub.2 .dbd.CH--C(O)--O--, CH.sub.2 .dbd.C(CH.sub.3)--C(O)--O--and 
##STR13## 
where the sum of ( n+m ) is an integer of 3 or more. 
In an eighth embodiment the present invention is directed to a 
polymerizable monomer represented by the formula (I), especially, the 
formula (VII) below, 
##STR14## 
wherein n is 2 or 3, R is selected from the group consisting of 
##STR15## 
and the substituent on the aromatic ring is present at the m-position or 
the p-position thereof. 
The inventors have found that run-away reactions can be easily controlled 
during polymerization; and polymerization time can be noticeably 
shortened. 
In addition, it has also been found that the resin of the present invention 
has a high surface hardness, i.e., scratch resistance, heat resistance and 
chemical resistance, and therefore plate materials comprising this resin 
are useful as glazing materials such as windowpanes in vehicles houses, 
schools and sports facilities, baseboards of verandas, and balconies, 
protective covers for display devices such as various dashboards, displays 
for computers, liquid crystal televisions and front boards of vending 
machines, and optical lenses. Furthermore, it has been found that the 
resin of the present invention is also useful as a coating film, i.e., 
hard coat material, because when the resin is applied onto a resin, a 
metal or a lumber material and then polymerized, the obtained hard coat 
has excellent scratch resistance and chemical resistance.

DESCRIPTION OF THE PREFERRED EMBODIMENTS 
Reference will now be made in detail to the present preferred embodiments 
of the invention. 
Exemplary suitable monomers (A) represented by the following formula (I) of 
the present invention 
##STR16## 
(wherein R is an aliphatic residue having or not having a halogen atom, an 
oxygen atom, an alicyclic ring, a heterocyclic ring or an aromatic ring, 
an alicyclic residue, or a heterocyclic residue, n is an integer of 1 to 
4, when n=1, X is oxygen or sulfur, when n.gtoreq.2, X's are all oxygen or 
all sulfur, one X is oxygen while the other X or X's are sulfur, one X is 
sulfur while the other X is X's are oxygen, or two X's are oxygen while 
the other X's are sulfur) include a carbamic acid ester or a thiocarbamic 
acid ester obtained by reacting isopropenyl-.alpha.,.alpha.-dimethylbenzyl 
isocyanate with a compound having from 1 to 4 OH groups or SH groups and 
an aliphatic residue which may or may not contain a halogen atom, an 
oxygen atom, an alicyclic ring, a heterocyclic ring or aromatic ring, an 
alicyclic residue or a heterocyclic residue, i.e., reacting the isocyanate 
group of isopropenyl-.alpha.,.alpha.-dimethylbenzyl isocyanate with the OH 
group or SH group. Here, compounds of the formula (I) where when n is 2 or 
more, X's are all oxygen or all sulfur, or when one or two X's are oxygen 
and the other X being sulfur, or one X is sulfur and the other X being 
oxygen, can be included. 
Usually, the lower the molecular weight of the residue R, the better, 
depending upon the steric firmness of its structure. Preferably, the 
molecular weight of the residue R is from 15 to 500. Exemplary suitable 
compounds having from 1 to 4 OH groups or SH groups and an aliphatic 
residue which may or may not have a halogen atom, an oxygen atom, an 
alicyclic ring, a heterocyclic ring or an aromatic ring, an alicyclic 
residue or a heterocyclic residue which are used in preparing the monomer 
(A) by the above-mentioned method include methanol, ethanol, propanol, 
butanol, pentanol, hexanol, heptanol, octanol, cyclopentanol, 
cyclohexanol, cycloheptanol, cyclooctanol, 2,2,2-trichloroethanol, 
2,2,2-trifluoroethanol, 1,3-dichloro-2-propanol, 2,3-dichloro-1-propanol, 
2,3-dibromo-1-propanol, 1-chloro-2-propanol, 3-chloro-1-propanol, 
2-chloroethanol, 2-bromoethanol, methanethiol, ethanethiol, propanethiol, 
butanethiol, pentanethiol, hexanethiol, heptanethiol, octanethiol, 
cyclohexanethiol, benzyl alcohol, ethylene glycol, 1,3-propanediol, 
1,4-butanediol, 1,4-butenediol, 1,5-pentanediol, 1,6-hexanediol, 
1,2-propanediol, 1,3-butanediol, 2,3-butanediol, 2,5-hexanediol, 
diethylene glycol, neopentyl glycol, 3-methyl-1,5-pentanediol, dipropylene 
glycol, triethylene glycol, 1,2-butanediol, 2-ethyl-1,3-hexanediol, spiro 
glycol, 1,4-cyclohexanediol, tricyclo[5,2,1,02,6]decane-4,8-dimethanol, 
3-chloro-1,2 -propanediol, 3-bromo-1,2 propanediol, 2,3-dibromo 
1,4-butanediol, dibromoneopentyl glycol, bisphenol A (2-hydroxyethyl) 
ether, bisphenol F (2-hydroxyethyl) ether, bisphenol S (2-hydroxyethyl) 
ether, biphenol (2-hydroxyethyl) ether, tetrabromobisphenol A 
(2-hydroxyethyl) ether, benzenedimethanol, ethanedithiol, propanedithiol, 
butanedithiol, pentanedithiol, hexanedithiol, propanetrithiol, 
eyclohexanedithiol, ethylene glycol bis(2-mercaptoacetate), ethylene 
glycol bis(3-mercaptopropionate), bis(mercaptomethyl)benzene, 
2-hydroxyethyl disulfide, 2-mercaptoethanol, 1-mercapto-2-propanol, 
glycerol, trimethylolethane, trimelthylolpropane, 1,2,4-butanetriol, 
1,2,6-hexanetriol, 1,3,5-tris(2-hydroxyethyl)cyanuric acid, 
pentaerythritol, threitol, 3-mercapto-1,2-propanediol, pentaerythritol 
tetrakis(2-mercapto acetate) and pentaerythritol tetrakis(3-mercapto 
propionate). The carbamic acid ester or thiocarbamic acid ester can be 
produced from the above-mentioned compounds by the reaction between the 
isocyanate group of isopropenyl-.alpha.,.alpha.-dimethylbenzyl isocyanate 
and the OH group or the SH group. At this time, a tin compound such as 
dibutyltin dilaurate, dimethyltin dichloride and the like or an amine such 
as morpholine, dimethylaminobenzene and the like may be added thereto as a 
catalyst to accelerate the synthetic reaction. Preferably, a tin compound 
is added to prevent coloring in a subsequent radical reaction. When a 
solvent is used, the solvent should be distilled off after completion of 
the synthetic reaction. If necessary, purification may be further carried 
out, and the thus obtained product may be used as the monomer (A) in the 
subsequent radical polymerization. 
Exemplary suitable monomers (A) for use in the invention include compounds 
represented by the formulae (IV), (V) and (VI): 
##STR17## 
wherein when n is 1, R is selected from the group consisting of 
--CH.sub.3, --C.sub.2 H.sub.5, --C.sub.3 H.sub.7, --C.sub.4 H.sub.9, 
--C.sub.5 H.sub.11, --C.sub.6 H.sub.13, --CH.sub.2 CCl.sub.3, --CH.sub.2 
CF.sub.3, 
##STR18## 
and the substituent on the aromatic ring is present at the m-position or 
the p-position thereof. 
##STR19## 
wherein when n is 2, R is selected from the group consisting of 
--(CH.sub.2)i --wherein i=2-6, 
##STR20## 
wherein i=1 or 2, 
##STR21## 
wherein i=0 or 2, --CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 --, 
##STR22## 
and the substituent on the aromatic ring is present at the m-position or 
the p-position thereof. 
##STR23## 
wherein when n is 3, R is selected from the group consisting of 
##STR24## 
and the substituent on the aromatic ring is present at the m-position or 
the p-position thereof. Further examples of the monomer (A) are: 
##STR25## 
(wherein n=4, R is 
##STR26## 
the substituents on the aromatic ring are at m- or p-position), 
##STR27## 
(wherein when n=2, R is --(CH.sub.2)i--(i=2-6), 
##STR28## 
the substituents on the aromatic ring are at m- or p-position), and 
##STR29## 
(wherein R2 is H or --CH.sub.3, the substituents on the aromatic ring are 
at m- or p-position). 
The monomer B having m functional groups of one kind selected from the 
group consisting of 
##STR30## 
in the present invention is an ester of acrylic acid or methacrylic acid 
or a derivative of styrene. Exemplary suitable monomers (B) in which m is 
1 for use in the invention include methyl acrylate, methyl methacrylate, 
ethyl acrylate, ethyl methacrylate, propyl acrylate, propyl methacrylate, 
isopropyl acrylate, isopropyl methacrylate, cyclohexyl acrylate, 
cyclohexyl methacrylate, benzyl acrylate, benzyl methacrylate, 
methoxyethyl acrylate, methoxyethyl methacrylate, ethoxyethyl acrylate, 
ethoxyethyl methacrylate, 2-hydroxyethyl acrylate, 2-hydroxyethyl 
methacrylate, 2-hydroxypropyl acrylate, 2-hydroxypropyl methacrylate, 
1,4-butylene glycol monoacrylate, 1,4-butylene glycol monomethacrylate, 
glycidyl acrylate, glycidyl methacrylate, styrene, methylstyrene, 
chlorostyrene, bromostyrene, chloromethylstyrene and methoxystyrene. 
Exemplary suitable monomers (B) in which m is 2 or more include ethylene 
glycol diacrylate, ethylene glycol dimethacrylate, diethylene glycol 
diacrylate, diethylene glycol dimethacrylate, propylene glycol diacrylate, 
propylene glycol dimethacrylate, dipropylene glycol diacrylate, 
dipropylene glycol dimethacrylate, 2,2-bis(4-acryloxyethoxyphenyl)propane, 
2,2-bis(4-methacryloxyethoxyphenyl)propane, 
2,2-bis(4-acryloxydiethoxyphenyl)propane, 
2,2-bis(4-methacryloxydiethoxyphenyl)propane, 
2,2-bis(4-acryloxypropyloxyphenyl)propane, 
2,2-bis(4-methacryloxypropyloxyphenyl)propane, 1,3-butanediol diacrylate, 
1,3-butanediol dimethacrylate, 1,4-butanediol diacrylate, 1,4-butanediol 
dimethacrylate, 1,6-hexanediol diacrylate, 1,6-hexanediol dimethacrylate, 
neopentyl glycol diacrylate, neopentyl glycol dimethacrylate, neopentyl 
glycol hydroxypivalate diacrylate, spiroglycol diacrylate, spiroglycol 
dimethacrylate, epoxy acrylate, epoxy methacrylate, 2-propenoic acid 
[2-[1,1-dimethyl-2-[(1-oxo-2-propenyl)oxy]ethyl]-5-ethyl-1,3-dioxane-5-yl] 
methyl ester, trimethylolpropane triacrylate, trimethylolpropane 
trimethacrylate, pentaerythritol triacrylate, pentaerythritol 
trimethacrylate, bis(acryloyloxyethyl)hydroxyethyl isocyanurate, 
bis(methacryloyloxyethyl)hydroxyethyl isocyanurate, tris(acryloyloxyethyl) 
isocyanurate, tris(methacryloyloxyethyl) isocyanurate, pentaerythritol 
tetraacrylate, pentaerythritol tetramethacrylate, dipentaerythritol 
hexaacrylate, dipentaerythritol hexamethacrylate, 
methyltri(acryloyloxyethoxy)silane, glycerol diacrylate, glycerol 
dimethacrylate, glycerol methacrylate acrylate, dibromoneopentyl glycol 
diacrylate, dibromoneopentyl glycol dimethacrylate, divinylbenzene, 
urethane acrylates, urethane methacrylates, 
1,1,3,3,5,5-hexa(acryloyloxy)cyclotriphosphazene, 
1,1,3,3,5,5-hexa(methacryloyloxy)cyclotriphosphazene, 
1,1,3,3,5,5-hexa(acryloylethylenedioxy)cyclotriphasphozene and 
1,1,3,3,5,5-hexa(methacryloylethylenedioxy)cyclotriphosphazene. 
In the present invention, the transparent resin having a high surface 
hardness can be prepared by copolymerizing a monomer (A) represented by 
the formula (I) 
##STR31## 
(wherein R is an aliphatic residue having or not having a halogen atom, an 
oxygen atom, an alicyclic ring, a heterocyclic ring or an aromatic ring, 
an alicyclic residue, or a heterocyclic residue, n is an integer of 1 to 
4, when n=1, X is oxygen or sulfur, when n.gtoreq.2, X's are all oxygen or 
all sulfur, one X is oxygen while the other X or X's are sulfur, one X is 
sulfur while the other X or X's are oxygen, or two (B) having, in one 
molecule, m functional groups of at least one kind selected from the group 
consisting of CH.sub.2 .dbd.CH--C(O)--O--, CH.sub.2 
.dbd.C(CH.sub.3)--C(O)--O--and 
##STR32## 
in such a ratio that (n+m) is an integer of 3 or more. 
For the purpose of adjusting viscosity and the like, a monomer having an 
isopropenylphenyl group other than the above-mentioned monomer (A) may be 
additionally used. 
Exemplary suitable additional monomers include diisoropenylbenzene, 
N-(3-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)-2-acryloyloxy carbamate 
and N-(3-isopropenyl-.alpha.,.alpha.-dimethltenzyl)-2-methacryloyloxy 
carbamate. 
In this copolymerization, the ratio of the isopropenyl group to 
##STR33## 
in the above-mentioned monomers depends on the type of functional groups 
in the monomers and the structures of the monomers, Preferably the 
copolymerization is carried out in a ratio of the isopropenylphenyl group: 
the total of 
##STR34## 
of 1 equivalent: 0.5-10 equivalents. 
The copolymerization in the present invention is a radical copolymerization 
and can be accomplished by heat polymerization or by a means using 
ultraviolet rays, .gamma.rays, or the like or a combination thereof. 
When the heat polymerization is carried out, the radical polymerization 
initiator is not limited to any particular one, but a known radical 
polymerization initiator can optionally be used, Exemplary suitable 
initiators include peroxides such as benzoyl peroxide, p-chlorobenzoyl 
peroxide, diisopropyl peroxy carbonate, di-2-ethylhexyl peroxy carbonate 
and carbonate and t-butylperoxy pivalate and an azo compound such as 
azobisisobutyronitrile. This initiator preferably used in an amount of 
from 0.01 to 5 % by weight. 
When the ultraviolet rays are utilized, the optical sensitizer is not 
particularly limited, but a known optical sensitizer can optionally be 
used. 
Exemplary suitable sensitizers include benzoyl compounds, tenzoin methyl 
ether, benzoin ethyl ether, benzoin propyl ether, benzoin isobutyl ether, 
2-hydroxy-2-benzoylpropane, azobisisobutyronitrile, benzil, thioxanthone 
and diphenyl disulfide. This sensitizer is preferably used in an amount of 
from 0.01 to 5 % by weight. When a radiation such as .gamma.ray and the 
like is utilized, the polymerization initiator and the like are not always 
necessary. 
In the present invention, the process for preparing plates or lenses of the 
high surface hardness, transparent resin is not particularly limited. 
Known processes can be used. A typical process is a casting polymerization 
process. For example, a mixture of the above-mentioned monomers is mixed 
with a radical polymerization initiator or an optical sensitizer 
sufficiently, followed by defoaming. Afterward, the mixture is poured into 
a glass or metallic mold with which a gasket or a spacer is combined, and 
is then cured by heating or the irradiation by ultraviolet rays or 
radiation. Additives may be added to the mixture prior to polymerization. 
Exemplary suitable additives include ultraviolet absorbents, oxidation 
inhibitors, dyes, infrared absorbents, release agents and antistatic 
agents. 
These additives should be used in amounts such that they do not prevent 
polymerization and curing. 
When the high surface hardness transparent resin is used for the 
preparation of coating films, a known coating film manufacturing process 
may be employed. For example, a radical polymerization initiator or an 
optical sensitizer is added to a mixture of the above-mentioned monomers, 
and if necessary, the mixture is diluted with a solvent. Afterward, a 
substrate made of a resin, a metal, a lumber material or the like is 
coated with the mixture by roll coating, spray coating, flow coating, 
dipping or the like. When the solvent is used, it is volatilized, and 
curing is then carried out by heating or by the irradiation by ultraviolet 
rays or radiation. In this case, additives, a filler and the like can be 
added to the mixture prior to the polymerization. Exemplary suitable 
additives include an ultraviolet absorbents, oxidation inhibitors, dyes, 
pigments, infrared absorbents, antistatic agents and fine inorganic 
compound grains. These additives should be used in amount such that they 
do not prevent the polymerization and curing. 
The thus obtained high surface hardness transparent resin plate can be used 
as a glazing material and a protective cover for display devices and has 
high scratch resistance, chemical resistance, heat resistance and 
excellent workability. In addition, when polymerization is carried out in 
a mold for lenses, or when the resin is processed by cutting and 
polishing, optical lenses having the same characteristics as in the above 
case can be obtained. 
Morever, the high-hardness transparent resin can be used as a coating 
material, i.e., a hard coat material that exhibits excellent scratch 
resistance, chemical resistance and the like on another resin, a metal, a 
lumber material or the like. 
The novel polymerizable monomer of the present invention is the 
above-mentioned monomer (A). Exemplary suitable polymerizable monomers 
include 
1,2-bis[N-(3-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)carbamoyloxy]ethan 
e, 
1,2-bis[N-(4-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)carbamoyloxy]ethan 
e, 
1-[N-(3-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)carbamoyloxy]-2-[N-(4-i 
sopropenyl-.alpha.,.alpha.-dimethylbenzyl)carbamoyloxy]ethane, 
1,3-bis[N-(3-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)carbamoyloxy]propa 
ne, 
1,3,-bis[N-(4-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)carbamoyloxy]prop 
ane, 
1-[N-(3-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)-carbamoyloxy]-3-[N-4-i 
sopropenyl-.alpha.,.alpha.-dimethylbenzyl)carbamoyloxy]propane, 
1,4-bis[N-(3-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)carbamoyloxy]butan 
e, 
1,4-bis[N-(4-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)carbamoyloxy]butan 
e, 
1-[N-(3-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)carbamoyloxy]-4-[N-(4-i 
sopropenyl-.alpha.,.alpha.-dimethylbenzyl)carbamoyloxy]butane, 
1,5-bis[N-(3-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)carbamoyloxy]penta 
ne, 
1,5-bis[N-(4-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)carbamoyloxy]penta 
ne, 
1-[N-(3-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)carbamoyloxy]-5-[N-(4-i 
sopropenyl-.alpha.,.alpha.-dimethylbenzyl)carbamoyloxy]pentane, 
1,6-bis[N-(3-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)carbamoyloxy]hexan 
e, 
1,6-bis[N-(4-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)carbamoyloxy]hexan 
e, 
1-[N-(3-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)carbamoyloxy]-6-[N-(4-i 
sopropenyl-.alpha.,.alpha.-dimethylbenzyl)carbamoyloxy]hexane, 
1,2-bis[N-(3-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)carbamoyloxy]-prop 
ane, 
1,2-bis[N-(4-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)carbamoyloxy]propa 
ne, 
1-[N-(3-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)carbamoyloxy]-2-[N-(4-i 
sopropenyl-.alpha.,.alpha.-dimethylbenzyl)carbamoyloxy]propane, 
1,3-bis[N-(3-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)carbamoyloxy]butan 
e, 
1,3-bis[N-(4-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)carbamoyloxy]butan 
e, 
1-[N-(3-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)carbamoyloxy]-3-(N-(4-i 
sopropenyl-.alpha.,.alpha.-dimethylbenzyl)carbamoyloxy]butane, 
2,3-bis[N-(3-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)carbamoyloxy]butan 
e, 
2,3-bis[N-(4-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)carbamoyloxy]butan 
e, 
2-[N-(3-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)carbamoyloxy]-3-[N-(4-i 
sopropenyl-.alpha.,.alpha.-dimethylbenzyl)carbamoyloxy]butane, 
2,5-bis[N-(3-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)carbamoyloxy]hexan 
e, 
2,5-bis[N-(4-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)carbamoyloxy]-hexa 
ne, 
2-[N-(3-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)carbamoyloxy]-5-[N-(4-i 
sopropenyl-.alpha.,.alpha.-dimethylbenzyl)carbamoyloxy]hexane, 
bis[2-(N-(3-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)carbamoyloxy)ethyl] 
ether, 
bis[2-(N-(4-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)carbamoyloxy)ethyl] 
ether, 
[2-(N-(3-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)carbamoyloxy)ethyl]-[2 
'-(N-(4-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)carbamoyloxy)ethyl]ether 
, 2,2-dimethyl-1,3-bis[N-(3-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)carb 
amoyloxy]-propane, 
2,2-dimethyl-1,3-bis[N-(4-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)carba 
moyloxy]propane, 
2,2-dimethyl-1-[N-(3-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)carbamoylo 
xy]-3-[N-(4-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)carbamoyloxy]propane 
, 3-methyl-1,5-bis[N-(3-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)carbamoy 
loxy]pentane, 
3-methyl-1,5-bis[N-(4-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)carbamoyl 
oxy]pentane, 
3-methyl-1-[N-(3-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)carbamoyloxy]- 
5-[N-(4-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)carbamoyloxy]pentane, 
bis[N-(3-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)carbamoyloxy)isopropyl 
]ether, 
bis[(N-(4-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)carbamoyloxy)isopropy 
l]ether, 
[(N-(3-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)carbamoyloxy)isopropyl][ 
(N-(4-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)carbamoyloxy) isopropyl] 
ether, 
bis[2-(N-(3-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)carbamoyloxy)ethoxy 
]ethane, 
bis[2-(N-(4-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)carbamoyloxy)ethoxy 
]ethane, 
[2-(N-(3-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)carbamoyloxy)ethoxy]-[ 
2'-(N-(4-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)carbamoyloxy)ethoxy]eth 
ane, 
1,2-bis[N-(3-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)carbamoyloxy]butan 
e, 
1,2-bis[N-(4-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)carbamoyloxy]butan 
e, 
1-[N-(3-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)carbamoyloxy]-2-[N-(4-i 
sopropenyl-.alpha.,.alpha.-dimethylbenzyl) carbamoyloxy]butane, 
1-[N-(4-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)carbamoyloxy]-2-[N-(3-i 
sopropenyl-.alpha.,.alpha.-dimethylbenzyl) carbamoyloxy]butane, 
2-ethyl-1,3-bis[N-(3-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)carbamoylo 
xy]hexane, 2-ethyl-1,3-bis[N-(4-isopropenyl-.alpha.,.alpha. 
-dimethylbenzyl)carbamoyloxy]hexane, 
2-ethyl-1-[N-(3-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)carbamoyloxy]-3 
-[N-(4-isopropenyl.alpha.,.alpha.-dimethylbenzyl)carbamoyloxy]hexane, 
2-ethyl-1-[N-(4-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)carbamoyloxy]-3 
-[N-(3-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)carbamoyloxy]hexane, 
3,9-bis[1,1-dimethyl-2-(N-(3-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)ca 
rbamoyloxy)ethyl]-2,4,8,10-tetraoxaspiro (5,5)undecane, 
3,9-bis[1,1-dimethyl-2-(N-(4-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)ca 
rbamoyloxy)ethyl]-2,4,8,10-tetraoxaspiro (5,5)undecane, 
3-[1,1-dimethyl-2-(N-(3-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)carbamo 
yloxy)ethyl]-9-[1,1-dimethyl-2-(N-(4-isopropenyl-.alpha.,.alpha.-dimethylbe 
nzyl)carbamoyloxy)ethyl]-2,4,8,10-tetraoxaspiro(5,5)-undecane, 
1,4-bis[N-(3-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)carbamoyloxy]cyclo 
hexane, 
1,4-bis[N-(4-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)carbamoyloxy]cyclo 
hexane, 
1-[N-(3-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)carbamoyloxy]-4-[N-(4-i 
sopropenyl-.alpha.,.alpha.-dimethylbenzyl) carbamoyloxy]cyclohexane, 
4,8-bis[N-(3-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)carbamoyloxymethyl 
]tricyclo]5,2,1,0.sup.2,6 ]decane, 
4,8-bis[N-(4-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)carbamoyloxymethyl 
]tricyclo[5,2,1,0.sup.2,6 ]decane, 
4-[N-(3-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)carbamoyloxymethyl]-8-[ 
N-(4-isopropenyl-.alpha.,.alpha.-dimethylbenzyl) 
carbamoyloxymethyl]tricyclo[5,2,1,0.sup.2,6 ]decane, 3-chloro-1,2 
bis[N-(3-isopropenyl-.alpha. ,.alpha.-dimethylbenzyl)carbamoyloxy]propane, 
3-chloro-1,2-bis[N-(4-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)carbamoyl 
oxy]propane, 
3-chloro-1-[N-(3-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)carbamoyloxy]- 
2-[N-(4-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)carbamoyloxy]propane, 
3-chloro-1-[N-(4-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)carbamoyloxy]- 
2-[N-(3-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)carbamoyloxy]propane, 
3-bromo-1,2-bis[N-(3-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)carbamoylo 
xy]propane, 
3-bromo-1,2-bis[N-(4-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)carbamoylo 
xy]propane, 
3-bromo-1-[N-(3-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)carbamoyloxy]-2 
-[N-(4-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)carbamoyloxy]propane, 
3-bromo-1-[N-(4-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)carbamoyloxy]-2 
-[N-(3-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)carbamoyloxy]propane, 
2,3-dibromo-1,4-bis[N-(3-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)carbam 
oyloxy]butane, 
2,3-dibromo-1,4-bis[N-(4-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)carbam 
oyloxy]butane, 
2,3-dibromo-1-[N-(3-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)carbamoylox 
y]-4-[N-(4-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)carbamoyloxy]butane, 
2,2-dibromomethyl-1,3-bis[N-(3-isopropenyl-.alpha.,.alpha.-dimethylbenzyl) 
carbamoyloxy]propane, 
2,2-dibromomethyl-1,3-bis[N-(4-isopropenyl-.alpha.,.alpha.-dimethylbenzyl) 
carbamoyloxy]propane, 
2,2-dibromomethyl-1-[N-(3-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)carba 
moyloxy]-3-[N-(4-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)carbamoyloxy]pr 
opane, 
1,2,3-tris[N-(3-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)carbamoyloxy]pr 
opane, 
1,2-bis[N-(3-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)carbamoyloxy]-3-[N 
-(4-isopropenyl-.alpha.,.alpha.-dimethylbenzyl) carbamoyloxy]propane, 
1,3-bis[N-(3-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)carbamoyloxy]-2-[ 
N-(4-isopropenyl-.alpha.,.alpha.-dimethylbenzyl) carbamoyloxy]propane, 
1,2-bis[N-(4-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)carbamoyloxy]-3-[N 
-(3-isopropenyl-.alpha.,.alpha.-dimethylbenzyl) carbamoyloxy]propane, 
1,3-bis[N-(4-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)carbamoyloxy]-2-[N 
-(3-isopropenyl-.alpha.,.alpha.-dimethylbenzyl) carbamoyloxy]propane, 
1,2,3-tris[N-(4-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)carbamoyloxy]pr 
opane, 
1,1,1-tris[N-(3-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)carbamoyloxymet 
hyl]ethane, 
1,1-bis[N-(3-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)carbamoyloxymethyl 
]-1-[N-(4-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)carbamoyloxymethyl]eth 
ane, 
1,1-bis[N-(4-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)carbamoyloxymethyl 
]-1-[N-(3-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)carbamoyloxymethyl]eth 
ane, 
1,1,1-tris[N-(4-ispropenyl-.alpha.,.alpha.-dimethylbenzyl)carbamoyloxymeth 
yl]ethane, 
2-ethyl-2-[N-(3-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)carbamoyloxymet 
hyl]-1,3-[N-(3-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)carbamoyloxy]prop 
ane, 
2-ethyl-2-[N-(4-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)carbamoyloxymet 
hyl]-1,3-[N-(3-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)carbamoyloxy]prop 
ane, 
2-ethyl-2-[N-(3-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)carbamoyloxymet 
hyl]-1,3-[N-(4-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)carbamoyloxy]prop 
ane, 
2-ethyl-2-[N-(4-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)carbamoyloxymet 
hyl]-1,3-[N-(4-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)carbamoyloxy]prop 
ane, 
1,2,4-tris[N-(3-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)carbamoyloxy]bu 
tane, 
1,2-bis[N-(3-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)carbamoyloxy]-4-[N 
-(4-isopropenyl-.alpha.,.alpha.-dimethylbenzyl) carbamoyloxy] butane, 
1,4-bis[N-(3-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)carbamoyloxy]-2-[N 
-(4-isopropenyl-.alpha.,.alpha.-dimethylbenzyl) carbamoyloxy]butane, 
1,2-bis[N-(4-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)carbamoyloxy]-4-[N 
-(3-isopropenyl-.alpha.,.alpha.-dimethylbenzyl) carbamoyloxy]butane, 
1,4-bis[N-(4-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)carbamoyloxy]-2-[N 
-(3-isopropenyl-.alpha.,.alpha.-dimethylbenzyl) carbamoyloxy]butane, 
1,2,4-tris[N-(4-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)carbamoyloxy]-b 
utane, 
1,3,5-tris[2-(N-(3-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)carbamoyloxy 
ethyl)]isocyanurate, 
1,3-bis[2-(N-(3-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)carbamoyloxyeth 
yl)]-5-[2-(N-(4-isopropenyl 
-.alpha.,.alpha.-dimethylbenzyl)carbamoyloxyethyl)]isocyanurate, 
1,3-bis[2-(N-(4-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)carbamoyloxyeth 
yl)]-5-[2-(N-(3-isopropenyl 
-.alpha.,.alpha.-dimethylbenzyl)carbamoyloxyethyl)]isocyanurate and 
1,3,5-tris[2-(N-(4-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)carbamoyloxy 
ethyl)]isocyanurate. 
The above-mentioned polymerizable monomer of the present invention can be 
prepared by the following procedure: A diol or a triol is allowed to react 
with 3-isopropenyl-.alpha.,.alpha.-dimethylbenzyl isocyanate, 
4-isopropenyl-.alpha.,.alpha.-dimethylbenzyl isocyanate or a mixture 
thereof in the absence or in the presence of a solvent and in the absence 
or in the presence of a catalyst at a suitable temperature. 
Exemplary suitable diols include ethylene glycol, 1,3-propanediol, 
1,4-butanediol, 1,5-pentanediol, 1,6-hexanediol, 1,2-propanediol, 
1,3-butanediol, 2,3-butanediol, 2,5-hexanediol, diethylene glycol, 
neopentyl glycol, 3-methyl-1,5-pentanediol, dipropylene glycol, 
triethylene glycol, 1,2-butanediol, 2-ethyl-1,3-hexanediol, 
3,9-bis(1,1-dimethyl-2-hydroxyethyl)-2,4,8,10-tetraoxaspiro(5,5)undecane, 
1,4-cyclohexanediol, tricyclo[5,2,1,0.sup.2,6 ]decane-4,8-dimethanol, 
3-chloro-1,2-propanediol, 3-bromo-1,2-propanediol, 
2,3-dibromo-1,4-butanediol and dibromoneopentyl glycol. Exemplary suitable 
triols include triglycerol, trimethylolethane, trimethylolpropane, 
1,2,4-butanetriol and 1,3,5-tris(2-hydroxyethyl)cyanuric acid. In this 
reaction, the amount of the 3-isopropenyl-.alpha.,.alpha.-dimethylbenzyl 
isocyanate, 4-isopropenyl-.alpha.,.alpha.-dimethylbenzyl isocyanate or a 
mixture thereof is preferably from 0.8 to 1.1 equivalents, more preferably 
0.95 to 1.05 equivalents per equivalent of the hydroxyl group in the diol 
or the triol. Furthermore, examples of the suitable solvent include 
hexane, chloroform, benzene, toluene and xylene which are not reactive 
with the raw materials. The above-mentioned suitable catalyst is a 
catalyst to accelerate a urethane formation reaction such as dibutyltin 
dilaurate and the like. The catalyst is preferably employed in an amount 
of from 0.01 to 5% by weight, preferably from 0.1 to 3% by weight based on 
the weight of the isocyanate. The suitable reaction temperature is 
preferably from about 30.degree. to 200.degree. C., more preferably from 
50.degree. to 150.degree. C. After completion of the reaction, the 
resulting reaction solution is then purified by column chromatography or 
another means, thereby obtaining the desired polymerizable monomer of the 
present invention. 
The resin of the present invention has a high surface hardness and is 
excellent in transparency, chemical resistance and heat resistance. In 
addition, it is also excellent in workability such as cutting owing to the 
high surface hardness. 
Moreover, in the preparation of the resin of the present invention, 
polymerization control in the polymerization step is very easy, and 
therefore any peeling, whiting and cracking do not occur in the molding 
polymerization. The resin of the present invention exhibits very good 
moldability and therefore accurate molding is possible. 
Thus, the resin of the present invention can be suitably used as a glazing 
material, a protective cover for display devices, an optical lens and a 
hard coat material. 
Furthermore, when the novel polymerizable monomer of the present invention 
is copolymerized with a monomer having a polymerizable group in which the 
polymerization rate is high, for example, an acrylic group, a methacrylic 
group or a vinylphenyl group, a transparent resin can be obtained which 
has a high surface hardness and which is excellent in heat resistance and 
workability such as cutting. Additionally, in the polymerization step, 
polymerization control is very easy. Therefore, the monomer of the present 
invention is useful as the raw material of the above-mentioned 
high-hardness transparent resin. 
The present invention will be further clarified by the following examples, 
which are intended to be purely exemplary of the invention. 
EXAMPLES 
In the following examples, part and parts are by weight, unless otherwise 
specified. 
EXAMPLE 1 
6.2 parts of ethylene glycol, 30 parts of toluene, 40.3 parts of 
3-isopropenyl-.alpha.,.alpha.-dimethylbenzyl isocyanate and 0.2 part of 
dibutyltin dilaurate were mixed. The solution was then stirred for 1 hour, 
while the temperature of the solution was maintained at 80.degree. C., to 
carry out the reaction. After completion of the reaction, the reaction 
solution was concentrated. The resulting concentrate was then purified by 
chromatography, thereby obtaining 40.0 parts of 
1,2-bis[N-(3-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)carbamoyloxy]ethan 
e in the form of colorless transparent liquid. 
______________________________________ 
Values of elemental analysis (as C.sub.28 H.sub.36 N.sub.2 O.sub.4) 
C H N 
______________________________________ 
Found (%) 72.13 7.59 6.21 
Calcd. (%) 72.39 7.81 6.03 
______________________________________ 
NMR(.delta./CDCl.sub.3) 
##STR35## 
##STR36## 
##STR37## 
##STR38## 
##STR39## 
##STR40## 
##STR41## 
##STR42## 
6.2 parts of ethylene glycol, 30 parts of toluene, 40.3 parts of 
4-isopropenyl-.alpha.,.alpha.-dimethylbenzyl isocyanate and 0.2 part of 
dibutyltin dilaurate were mixed. The mixed solution was then stirred for 1 
hour, while the temperature of the solution was maintained at 80.degree. 
C., to carry out the reaction. After completion of the reaction, the 
reaction solution was concentrated. The concentrated solution was then 
purified by chromatography, thereby obtaining 41.2 parts of 
1,2-bis[N-(4-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)carbamoyloxy]ethan 
e in the form of a colorless transparent liquid. 
______________________________________ 
Values of elemental analysis (as C.sub.28 H.sub.36 N.sub.2 O.sub.4) 
C H N 
______________________________________ 
Found (%) 72.59 7.92 6.18 
Calcd. (%) 72.39 7.81 6.03 
______________________________________ 
NMR(.delta./CDCl.sub.3) 
##STR43## 
##STR44## 
##STR45## 
##STR46## 
##STR47## 
##STR48## 
##STR49## 
The same procedure as in Example 1 was repeated except that 6.2 parts of 
ethylene glycol was replaced with 7.6 parts of 1,3-propanediol, thereby 
obtaining 42.5 parts of 
1,3-bis[N-(3-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)carbamoyloxy]propa 
ne in the form of a colorless transparent liquid. 
______________________________________ 
Values of elemental analysis (as C.sub.29 H.sub.38 N.sub.2 O.sub.4) 
C H N 
______________________________________ 
Found (%) 72.71 7.81 5.69 
Calcd. (%) 72.77 8.00 5.85 
______________________________________ 
NMR(.delta./CDCl.sub.3) 
##STR50## 
##STR51## 
##STR52## 
##STR53## 
##STR54## 
##STR55## 
##STR56## 
##STR57## 
The same procedure as in Example 2 was repeated except that 6.2 parts of 
ethylene glycol was replaced with 7.6 parts of 1,3-propanediol, thereby 
obtaining 41.7 parts of 
1,3-bis[N-(4-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)carbamoyloxy]propa 
ne in the form of a colorless transparent liquid. 
______________________________________ 
Values of elemental analysis (as C.sub.29 H.sub.38 N.sub.2 O.sub.4) 
C H N 
______________________________________ 
Found (%) 72.98 8.13 5.53 
Calcd. (%) 72.77 8.00 5.85 
______________________________________ 
NMR(.delta./CDCl.sub.3) 
##STR58## 
##STR59## 
##STR60## 
##STR61## 
##STR62## 
##STR63## 
##STR64## 
The same procedure as in Example 1 was repeated except that 6.2 parts of 
ethylene glycol was replaced with 9.0 parts of 1,4-butanediol, thereby 
obtaining 44.4 parts of 
1,4-bis[N-(3-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)carbamoyloxy]butan 
e in the form of a colorless transparent liquid. 
______________________________________ 
Values of elemental analysis (as C.sub.30 H.sub.40 N.sub.2 O.sub.4) 
C H N 
______________________________________ 
Found (%) 72.88 8.23 5.47 
Calcd. (%) 73.14 8.18 5.69 
______________________________________ 
NMR(.delta./CDCl.sub.3) 
##STR65## 
##STR66## 
##STR67## 
##STR68## 
##STR69## 
##STR70## 
##STR71## 
##STR72## 
EXAMPLE 6 The same procedure as in Example 2 was repeated except that 
6.2 parts of ethylene glycol was replaced with 9.0 parts of 
1,4-butanediol, thereby obtaining 43.9 parts of 1,4-bis[N-(4-isopropenyl-. 
alpha.,.alpha.-dimethylbenzyl)carbamoyloxy]butane in the form of a 
colorless transparent liquid. 
______________________________________ 
Values of elemental analysis (as C.sub.30 H.sub.40 N.sub.2 O.sub.4) 
C H N 
______________________________________ 
Found (%) 73.29 7.96 5.73 
Calcd. (%) 73.14 8.18 5.69 
______________________________________ 
NMR(.delta./CDCl.sub.3) 
##STR73## 
##STR74## 
##STR75## 
##STR76## 
##STR77## 
##STR78## 
##STR79## 
The same procedure as in Example 1 was repeated except that 6.2 parts of 
ethylene glycol was replaced with 10.4 parts of 1,5-pentanediol, thereby 
obtaining 44.6 parts of 
1,5-bis[N-(3-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)carbamoyloxy]penta 
ne in the form of a colorless transparent liquid. 
______________________________________ 
Values of elemental analysis (as C.sub.31 H.sub.42 N.sub.2 O.sub.4) 
C H N 
______________________________________ 
Found (%) 73.53 8.47 5.36 
Calcd. (%) 73.49 8.35 5.53 
______________________________________ 
NMR(.delta./CDCl.sub.3) 
##STR80## 
##STR81## 
##STR82## 
##STR83## 
##STR84## 
##STR85## 
##STR86## 
##STR87## 
The same procedure as in Example 2 was repeated except that 6.2 parts of 
ethylene glycol was replaced with 10.4 parts of 1,5-pentanediol, thereby 
obtaining 43.6 parts of 
1,5-bis[N-(4-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)carbamoyloxy]penta 
ne in the form of a colorless transparent liquid. 
______________________________________ 
Values of elemental analysis (as C.sub.31 H.sub.42 N.sub.2 O.sub.4) 
C H N 
______________________________________ 
Found (%) 73.88 8.19 5.74 
Calcd. (%) 73.49 8.35 5.53 
______________________________________ 
NMR(.delta./CDCl.sub.3) 
##STR88## 
##STR89## 
##STR90## 
##STR91## 
##STR92## 
##STR93## 
##STR94## 
The same procedure as in Example 1 was repeated except that 6.2 parts of 
ethylene glycol was replaced with 11.8 parts of 1,6-hexanediol, thereby 
obtaining 48.5 parts of 
1,6-bis[N-(3-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)carbamoyloxy]-hexa 
ne in the form of a colorless transparent liquid. 
______________________________________ 
Values of elemental analysis (as C.sub.32 H.sub.44 N.sub.2 O.sub.4) 
C H N 
______________________________________ 
Found (%) 73.98 8.43 5.51 
Calcd. (%) 73.81 8.52 5.38 
______________________________________ 
NMR(.delta./CDCl.sub.3) 
##STR95## 
##STR96## 
##STR97## 
##STR98## 
##STR99## 
##STR100## 
##STR101## 
##STR102## 
The same procedure as in Example 2 was repeated except that 6.2 parts of 
ethylene glycol was replaced with 11.8 parts of 1,6-hexanediol, thereby 
obtaining 47.7 parts of 
1,6-bis[N-(4-isopropenyl)-.alpha.,.alpha.-dimethylbenzyl)carbamoyloxy]hexa 
ne in the form of a colorless transparent liquid. 
______________________________________ 
Values of elemental analysis (as C.sub.32 H.sub.44 N.sub.2 O.sub.4) 
C H N 
______________________________________ 
Found (%) 73.97 8.61 5.14 
Calcd. (%) 73.81 8.52 5.38 
______________________________________ 
NMR(.delta./CDCl.sub.3) 
##STR103## 
##STR104## 
##STR105## 
##STR106## 
##STR107## 
##STR108## 
##STR109## 
The same procedure as in Example 1 was repeated except that 6.2 parts of 
ethylene glycol was replaced with 7.6 parts of 1,2-propanediol, thereby 
obtaining 43.1 parts of 
1,2-bis[N-(3-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)carbamoyloxy]propa 
ne in the form of a colorless transparent liquid. 
______________________________________ 
Values of elemental analysis (as C.sub.29 H.sub.38 N.sub.2 O.sub.4) 
C H N 
______________________________________ 
Found (%) 72.63 8.15 5.67 
Calcd. (%) 72.77 8.00 5.85 
______________________________________ 
NMR(.delta./CDCl.sub.3) 
##STR110## 
##STR111## 
##STR112## 
##STR113## 
##STR114## 
##STR115## 
##STR116## 
##STR117## 
##STR118## 
The same procedure as in Example 2 was repeated except that 6.2 parts of 
ethylene glycol was replaced with 7.6 parts of 1,2-propanediol, thereby 
obtaining 44.8 parts of 
1,2-bis[N-(4-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)carbamoyloxy]propa 
ne in the form of a colorless transparent liquid. 
______________________________________ 
Values of elemental analysis (as C.sub.29 H.sub.38 N.sub.2 O.sub.4) 
C H N 
______________________________________ 
Found (%) 72.69 8.15 5.72 
Calcd. (%) 72.77 8.00 5.85 
______________________________________ 
NMR(.delta./CDCl.sub.3) 
##STR119## 
##STR120## 
##STR121## 
##STR122## 
##STR123## 
##STR124## 
##STR125## 
##STR126## 
The same procedure as in Example 1 was repeated except that 6.2 parts of 
ethylene glycol was replaced with 9.0 parts of 1,3-butanediol, thereby 
obtaining 45.2 parts of 
1,3-bis[N-(3-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)carbamoyloxy]butan 
e in the form of a colorless transparent liquid. 
______________________________________ 
Values of elemental analysis (as C.sub.30 H.sub.40 N.sub.2 O.sub.4) 
C H N 
______________________________________ 
Found (%) 72.98 7.87 5.81 
Calcd. (%) 73.14 8.18 5.69 
______________________________________ 
NMR(.delta./CDCl.sub.3) 
##STR127## 
##STR128## 
##STR129## 
##STR130## 
##STR131## 
##STR132## 
##STR133## 
##STR134## 
##STR135## 
##STR136## 
EXAMPLE 14 The same procedure as in Example 2 was replaced except that 
6.2 parts of ethylene glycol was replaced with 9.0 parts of 
1,3-butanediol, thereby obtaining 46.7 parts of 1,3-bis[N-(4-isopropenyl-. 
alpha.,.alpha.-dimethylbenzyl)carbamoyloxy]butane in the form of a 
colorless transparent liquid. 
______________________________________ 
Values of elemental analysis (as C.sub.30 H.sub.40 N.sub.2 O.sub.4) 
C H N 
______________________________________ 
Found (%) 73.37 8.03 5.86 
Calcd. (%) 73.14 8.18 5.69 
______________________________________ 
NMR(.delta./CDCl.sub.3) 
##STR137## 
##STR138## 
##STR139## 
##STR140## 
##STR141## 
##STR142## 
##STR143## 
##STR144## 
The same procedure as in Example 1 was repeated except that 6.2 parts of 
ethylene glycol was replaced with 9.0 parts of 2,3-butanediol, thereby 
obtaining 44.8 parts of 
2,3-bis[N-(3-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)carbamoyloxy]butan 
e in the form of a colorless transparent liquid. 
______________________________________ 
Values of elemental analysis (as C.sub.30 H.sub.40 N.sub.2 O.sub.4) 
C H N 
______________________________________ 
Found (%) 73.01 8.29 5.42 
Calcd. (%) 73.14 8.18 5.69 
______________________________________ 
NMR(.delta./CDCl.sub.3) 
##STR145## 
##STR146## 
##STR147## 
##STR148## 
##STR149## 
##STR150## 
##STR151## 
##STR152## 
##STR153## 
The same procedure as in Example 2 was repeated except that 6.2 parts of 
ethylene glycol was replaced with 9.0 parts of 2,3-butanediol, thereby 
obtaining 42.9 parts of 
2,3-bis[N-(4-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)carbamoyloxy]butan 
e in the form of a colorless transparent liquid. 
______________________________________ 
Values of elemental analysis (as C.sub.30 H.sub.40 N.sub.2 O.sub.4) 
C H N 
______________________________________ 
Found (%) 73.44 8.09 5.47 
Calcd. (%) 73.14 8.18 5.69 
______________________________________ 
NMR(.delta./CDCl.sub.3) 
##STR154## 
##STR155## 
##STR156## 
##STR157## 
##STR158## 
##STR159## 
##STR160## 
##STR161## 
The same procedure as in Example 1 was repeated except that 6.2 parts of 
ethylene glycol was replaced with 11.8 parts of 2,5-hexanediol, thereby 
obtaining 49.1 parts of 
2,5-bis[N-(3-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)carbamoyloxy]hexan 
e in the form of a colorless transparent liquid. 
______________________________________ 
Values of elemental analysis (as C.sub.32 H.sub.44 N.sub.2 O.sub.4) 
C H N 
______________________________________ 
Found (%) 73.98 8.36 5.14 
Calcd. (%) 73.81 8.52 5.38 
______________________________________ 
NMR(.delta./CDCl.sub.3) 
##STR162## 
##STR163## 
##STR164## 
##STR165## 
##STR166## 
##STR167## 
##STR168## 
##STR169## 
The same procedure as in Example 2 was repeated except that 6.2 parts of 
ethylene glycol was replaced with 11.8 parts of 2,5-hexanediol, thereby 
obtaining 47.9 parts of 
2,5-bis[N-(4-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)carbamoyloxy]hexan 
e in the form of a colorless transparent liquid. 
______________________________________ 
Values of elemental analysis (as C.sub.32 H.sub.44 N.sub.2 O.sub.4) 
C H N 
______________________________________ 
Found (%) 74.03 8.77 5.28 
Calcd. (%) 73.81 8.52 5.38 
______________________________________ 
NMR(.delta./CDCl.sub.3) 
##STR170## 
##STR171## 
##STR172## 
##STR173## 
##STR174## 
##STR175## 
##STR176## 
The same procedure as in Example 1 was repeated except that 6.2 parts of 
ethylene glycol was replaced with 10.6 parts of diethylene glycol, thereby 
obtaining 47.4 parts of 
bis[2-(N-(3-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)carbamoyloxy)ethyl] 
ether in the form of a colorless transparent liquid. 
______________________________________ 
Values of elemental analysis (as C.sub.30 H.sub.40 N.sub.2 O.sub.5) 
C H N 
______________________________________ 
Found (%) 70.66 7.72 5.68 
Calcd. (%) 70.84 7.93 5.51 
______________________________________ 
NMR(.delta./CDCl.sub.3) 
##STR177## 
##STR178## 
##STR179## 
##STR180## 
##STR181## 
##STR182## 
##STR183## 
##STR184## 
The same procedure as in Example 2 was repeated except that 6.2 parts of 
ethylene glycol was replaced with 10.6 parts of diethylene glycol, thereby 
obtaining 47.6 parts of 
bis[2-(N-(4-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)carbamoyloxy)ethyl] 
ether in the form of a colorless transparent liquid. 
______________________________________ 
Values of elemental analysis (as C.sub.30 H.sub.40 N.sub.2 O.sub.5) 
C H N 
______________________________________ 
Found (%) 70.79 7.98 5.38 
Calcd. (%) 70.84 7.93 5.51 
______________________________________ 
NMR(.delta./CDCl.sub.3) 
##STR185## 
##STR186## 
##STR187## 
##STR188## 
##STR189## 
##STR190## 
##STR191## 
##STR192## 
The same procedure as in Example 1 was repeated except that 6.2 parts of 
ethylene glycol was replaced with 10.4 parts of neopentyl glycol, thereby 
obtaining 46.9 parts of 
2,2-dimethyl-1,3-bis[N-(3-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)carba 
moyloxy]propane in the form of a colorless transparent liquid. 
______________________________________ 
Values of elemental analysis (as C.sub.31 H.sub.42 N.sub.2 O.sub.4) 
C H N 
______________________________________ 
Found (%) 73.38 8.34 5.74 
Calcd. (%) 73.49 8.35 5.53 
______________________________________ 
NMR(.delta./CDCl.sub.3) 
##STR193## 
##STR194## 
##STR195## 
##STR196## 
##STR197## 
##STR198## 
##STR199## 
##STR200## 
##STR201## 
The same procedure as in Example 2 was repeated except that 6.2 parts of 
ethylene glycol was replaced with 10.4 parts of neopentyl glycol, thereby 
obtaining 48.1 parts of 
2,2-dimethyl-1,3-bis[N-(4-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)carba 
moyloxy]propane in the form of a colorless transparent liquid. 
______________________________________ 
Values of elemental analysis (as C.sub.31 H.sub.42 N.sub.2 O.sub.4) 
C H N 
______________________________________ 
Found (%) 73.18 8.42 5.71 
Calcd. (%) 73.49 8.35 5.53 
______________________________________ 
NMR(.delta./CDCl.sub.3) 
##STR202## 
##STR203## 
##STR204## 
##STR205## 
##STR206## 
##STR207## 
##STR208## 
##STR209## 
The same procedure as in Example 1 was repeated except that 6.2 parts of 
ethylene glycol was replaced with 11.8 parts of 3-methyl-1,5-pentanediol, 
thereby obtaining 47.7 parts of 
3-methyl-1,5-bis[N-(3-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)carbamoyl 
oxy]pentane in the form of a colorless transparent liquid. 
______________________________________ 
Values of elemental analysis (as C.sub.32 H.sub.44 N.sub.2 O.sub.4) 
C H N 
______________________________________ 
Found (%) 73.67 8.74 5.36 
Calcd. (%) 73.81 8.52 5.38 
______________________________________ 
NMR(.delta./CDCl.sub.3) 
##STR210## 
##STR211## 
##STR212## 
##STR213## 
##STR214## 
##STR215## 
##STR216## 
##STR217## 
##STR218## 
The same procedure as in Example 2 was repeated except that 6.2 parts of 
ethylene glycol was replaced with 11.8 parts of 3-methyl-1,5-pentanediol, 
thereby obtaining 46.8 parts of 
3-methyl-1,5-bis[N-(4-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)carbamoyl 
oxy]pentane in the form of a colorless transparent liquid. 
______________________________________ 
Values of elemental analysis (as C.sub.32 H.sub.44 N.sub.2 O.sub.4) 
C H N 
______________________________________ 
Found (%) 73.93 8.76 5.24 
Calcd. (%) 73.81 8.52 5.38 
______________________________________ 
NMR(.delta./CDCl.sub.3) 
##STR219## 
##STR220## 
##STR221## 
##STR222## 
##STR223## 
##STR224## 
##STR225## 
##STR226## 
The same procedure as in Example 1 was repeated except that 6.2 parts of 
ethylene glycol was replaced with 13.4 parts of dipropylene glycol, 
thereby obtaining 49.7 parts of 
bis[(N-(3-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)carbamoyloxy(isopropy 
l] ether in the form of a colorless transparent liquid. 
______________________________________ 
Values of elemental analysis (as C.sub.32 H.sub.44 N.sub.2 O.sub.5) 
C H N 
______________________________________ 
Found (%) 71.78 8.14 5.06 
Calcd. (%) 71.61 8.26 5.22 
______________________________________ 
NMR(.delta./CDCl.sub.3) 
##STR227## 
##STR228## 
##STR229## 
##STR230## 
##STR231## 
##STR232## 
##STR233## 
##STR234## 
##STR235## 
##STR236## 
##STR237## 
##STR238## 
##STR239## 
##STR240## 
##STR241## 
##STR242## 
##STR243## 
##STR244## 
##STR245## 
##STR246## 
##STR247## 
##STR248## 
##STR249## 
##STR250## 
##STR251## 
##STR252## 
##STR253## 
##STR254## 
##STR255## 
##STR256## 
##STR257## 
The same procedure as in Example 2 was repeated except that 6.2 parts of 
ethylene glycol was replaced with 13.4 parts of dipropylene glycol, 
thereby obtaining 50.6 parts of 
bis[(N-(4-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)carbamoyloxy)isopropy 
l] ether in the form of a colorless transparent liquid (a mixture is 
isomers). 
______________________________________ 
Values of elemental analysis (as C.sub.32 H.sub.44 N.sub.2 O.sub.5) 
C H N 
______________________________________ 
Found (%) 71.77 8.05 5.38 
Calcd. (%) 71.61 8.26 5.22 
______________________________________ 
NMR(.delta./CDCl.sub.3) 
##STR258## 
##STR259## 
##STR260## 
##STR261## 
##STR262## 
##STR263## 
##STR264## 
##STR265## 
##STR266## 
##STR267## 
##STR268## 
##STR269## 
##STR270## 
##STR271## 
##STR272## 
##STR273## 
##STR274## 
##STR275## 
##STR276## 
##STR277## 
##STR278## 
##STR279## 
##STR280## 
##STR281## 
##STR282## 
##STR283## 
##STR284## 
##STR285## 
The same procedure as in Example 1 was repeated except that 6.2 parts of 
ethylene glycol was replaced with 15.0 parts of triethylene glycol, 
thereby obtaining 49.5 parts of 
bis[2-(N-(3-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)carbamoyloxy)ethoxy 
]ethane in the form of a colorless transparent liquid. 
______________________________________ 
Values of elemental analysis (as C.sub.32 H.sub.44 N.sub.2 O.sub.6) 
C H N 
______________________________________ 
Found (%) 69.62 8.31 4.93 
Calcd. (%) 69.54 8.02 5.07 
______________________________________ 
NMR(.delta./CDCl.sub.3) 
##STR286## 
##STR287## 
##STR288## 
##STR289## 
##STR290## 
##STR291## 
##STR292## 
##STR293## 
##STR294## 
The same procedure as in Example 2 was repeated except that 6.2 parts of 
ethylene glycol was replaced with 15.0 parts of triethylene glycol, 
thereby obtaining 51.5 parts of 
bis[2-(N-(4-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)carbamoyloxy)ethoxy 
]ethane in the form of a colorless transparent liquid. 
______________________________________ 
Values of elemental analysis (as C.sub.32 H.sub.44 N.sub.2 O.sub.6) 
C H N 
______________________________________ 
Found (%) 69.61 8.29 5.09 
Calcd. (%) 69.54 8.02 5.07 
______________________________________ 
NMR(.delta./CDCl.sub.3) 
##STR295## 
##STR296## 
##STR297## 
##STR298## 
##STR299## 
##STR300## 
##STR301## 
##STR302## 
The same procedure as in Example 1 was repeated except that 6.2 parts of 
ethylene glycol was replaced with 9.0 parts of 1,2-butanediol, thereby 
obtaining 43.4 parts of 
1,2-bis[N-(3-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)carbamoyloxy]butan 
e in the form of a colorless transparent liquid. 
______________________________________ 
Values of elemental analysis (as C.sub.30 H.sub.40 N.sub.2 O.sub.4) 
C H N 
______________________________________ 
Found (%) 72.98 8.34 5.47 
Calcd. (%) 73.14 8.18 5.69 
______________________________________ 
NMR(.delta./CDCl.sub.3) 
##STR303## 
##STR304## 
##STR305## 
##STR306## 
##STR307## 
##STR308## 
##STR309## 
##STR310## 
##STR311## 
The same procedure as in Example 2 was repeated except that 6.2 parts of 
ethylene glycol was replaced with 9.0 parts of 1,2-butanediol, thereby 
obtaining 46.4 parts of 
1,2-bis[N-(4-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)carbamoyloxy]butan 
e in the form of a colorless transparent liquid. 
______________________________________ 
Values of elemental analysis (as C.sub.30 H.sub.40 N.sub.2 O.sub.4) 
C H N 
______________________________________ 
Found (%) 73.18 8.07 5.43 
Calcd. (%) 73.14 8.18 5.69 
______________________________________ 
NMR(.delta./CDCl.sub.3) 
##STR312## 
##STR313## 
##STR314## 
##STR315## 
##STR316## 
##STR317## 
##STR318## 
##STR319## 
The same procedure as in Example 1 was repeated except that 6.2 parts of 
ethylene glycol was replaced with 14.6 parts of 2-ethyl-1,3-hexanediol, 
thereby obtaining 50.4 parts of 
2-ethyl-1,3-bis[N-(3-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)carbamoylo 
xy]hexane in the form of a colorless transparent liquid. 
______________________________________ 
Values of elemental analysis (as C.sub.34 H.sub.48 N.sub.2 O.sub.4) 
C H N 
______________________________________ 
Found (%) 74.56 8.77 5.04 
Calcd. (%) 74.42 8.82 5.10 
______________________________________ 
NMR(.delta./CDCl.sub.3) 
##STR320## 
##STR321## 
##STR322## 
##STR323## 
##STR324## 
##STR325## 
##STR326## 
##STR327## 
The same procedure as in Example 2 was repeated except that 6.2 parts of 
ethylene glycol was replaced with 14.6 parts of 2-ethyl-1,3-hexanediol, 
thereby obtaining 51.1 parts of 
2-ethyl-1,3-bis[N-(4-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)carbamoylo 
xy]hexane in the form of a colorless transparent liquid. 
______________________________________ 
Values of elemental analysis (as C.sub.34 H.sub.48 N.sub.2 O.sub.4) 
C H N 
______________________________________ 
Found (%) 74.47 8.73 5.16 
Calcd. (%) 74.42 8.82 5.10 
______________________________________ 
NMR(.delta./CDCl.sub.3) 
##STR328## 
##STR329## 
##STR330## 
##STR331## 
##STR332## 
##STR333## 
##STR334## 
The same procedure as in Example 1 was repeated except that 6.2 parts of 
ethylene glycol was replaced with 30.4 parts of 
3,9-bis(1,1-dimethyl-2-hydroxyethyl]-2,4,8,10-tetraoxaspiro(5,5)undecane, 
thereby obtaining 66.7 parts of 
3,9-bis[1,1-dimethyl-2-(N-(3-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)ca 
rbamoyloxy)ethyl]-2,4,8,10-tetraoxaspiro (5,5)undecane in the form of a 
colorless transparent liquid. 
______________________________________ 
Values of elemental analysis (as C.sub.41 H.sub.58 N.sub.2 O.sub.8) 
C H N 
______________________________________ 
Found (%) 69.56 8.34 3.72 
Calcd. (%) 69.66 8.27 3.96 
______________________________________ 
NMR(.delta./CDCl.sub.3) 
##STR335## 
##STR336## 
##STR337## 
##STR338## 
##STR339## 
##STR340## 
##STR341## 
##STR342## 
##STR343## 
##STR344## 
The same procedure as in Example 2 was repeated except that 6.2 parts of 
ethylene glycol was replaced with 30.4 parts of 
3,9-bis(1,1-dimethyl-2-hydroxyethyl]-2,4,8,10-tetraoxaspiro(5,5)undecane, 
thereby obtaining 63.4 parts of 
3,9-bis[1,1-dimethyl-2-(N-(4-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)ca 
rbamoyloxy)ethyl]-2,4,8,10-tetraoxaspiro (5,5)undecane in the form of a 
colorless transparent liquid. 
______________________________________ 
Values of elemental analysis (as C.sub.41 H.sub.58 N.sub.2 O.sub.8) 
C H N 
______________________________________ 
Found (%) 69.73 8.48 3.75 
Calcd. (%) 69.66 8.27 3.96 
______________________________________ 
NMR(.delta./CDCl.sub.3) 
##STR345## 
##STR346## 
##STR347## 
##STR348## 
##STR349## 
##STR350## 
##STR351## 
##STR352## 
##STR353## 
The same procedure as in Example 1 was repeated except that 6.2 parts of 
ethylene glycol was replaced with 11.6 parts of 1,4-cyclohexanediol, 
thereby obtaining 48.2 parts of 
1,4-bis[N-(3-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)carbamoyloxy]cyclo 
hexane in the form of a colorless transparent liquid. 
______________________________________ 
Values of elemental analysis (as C.sub.32 H.sub.42 N.sub.2 O.sub.4) 
C H N 
______________________________________ 
Found (%) 74.23 8.05 5.62 
Calcd. (%) 74.10 8.16 5.40 
______________________________________ 
NMR(.delta./CDCl.sub.3) 
##STR354## 
##STR355## 
##STR356## 
##STR357## 
##STR358## 
##STR359## 
##STR360## 
The same procedure as in Example 2 was repeated except that 6.2 parts of 
ethylene glycol was replaced with 11.6 parts of 1,4-cyclohexanediol, 
thereby obtaining 46.7 parts of 
1,4-bis[N-(4-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)carbamoyloxy]cyclo 
hexane in the form of a colorless transparent liquid. 
______________________________________ 
Values of elemental analysis (as C.sub.32 H.sub.42 N.sub.2 O.sub.4) 
C H N 
______________________________________ 
Found (%) 74.35 8.32 5.29 
Calcd. (%) 74.10 8.16 5.40 
______________________________________ 
NMR(.delta./CDCl.sub.3) 
##STR361## 
##STR362## 
##STR363## 
##STR364## 
##STR365## 
##STR366## 
##STR367## 
The same procedure as in Example 1 was repeated except that 6.2 parts of 
ethylene glycol was replaced with 19.6 parts of tricyclo[5,2,1,0.sup.2,6 
]decane-4,8-dimethanol, thereby obtaining 55.9 parts of 
4,8-bis[N-(3-isopropenyl-.alpha.,.alpha.-dimethylbezyl)carbamoyloxymethyl] 
tricyclo [5,2,1,0.sup.2,6 ]decane in the form of a colorless transparent 
liquid. 
______________________________________ 
Values of elemental analysis (as C.sub.38 H.sub.50 N.sub.2 O.sub.4) 
C H N 
______________________________________ 
Found (%) 76.27 8.69 4.55 
Calcd. (%) 76.22 8.42 4.68 
______________________________________ 
NMR(.delta./CDCl.sub.3) 
##STR368## 
##STR369## 
##STR370## 
##STR371## 
##STR372## 
##STR373## 
##STR374## 
The same procedure as in Example 2 was repeated except that 6.2 parts of 
ethylene glycol was replaced with 19.6 parts of tricyclo[5,2,1,0.sup.2,6 
]decane-4,8-dimethanol, thereby obtaining 54.8 parts of 
4,8-bis[N-(4-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)carbamoylmethyl]tr 
icyclo[5,2,1,0.sup.2,6 decane in the form of a colorless transparent 
liquid. 
______________________________________ 
Values of elemental analysis (as C.sub.38 H.sub.50 N.sub.2 O.sub.4) 
C H N 
______________________________________ 
Found (%) 76.19 8.65 4.32 
Calcd. (%) 76.22 8.42 4.68 
______________________________________ 
NMR(.delta./CDCl.sub.3) 
##STR375## 
##STR376## 
##STR377## 
##STR378## 
##STR379## 
##STR380## 
The same procedure as in Example 1 was repeated except that 6.2 parts of 
ethylene glycol was replaced with 11.1 parts of 3-chloro-1,2-propanediol, 
thereby obtaining 49.2 parts of 
3-chloro-1,2-bis[N-(3-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)carbamoyl 
oxy]propane in the form of a colorless transparent liquid. 
______________________________________ 
Values of elemental analysis (as C.sub.29 H.sub.37 N.sub.2 O.sub.4 Cl) 
C H N Cl 
______________________________________ 
Found (%) 67.72 7.31 5.35 6.98 
Calcd. (%) 67.89 7.27 5.46 6.91 
______________________________________ 
NMR(.delta./CDCl.sub.3) 
##STR381## 
##STR382## 
##STR383## 
##STR384## 
##STR385## 
##STR386## 
##STR387## 
##STR388## 
The same procedure as in Example 2 was repeated except that 6.2 parts of 
ethylene glycol was replaced with 11.1 parts of 3-chloro-1,2-propanediol, 
thereby obtaining 49.8 parts of 
3-chloro-1,2-bis[N-(4-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)carbamoyl 
oxy]propane in the form of a colorless transparent liquid. 
______________________________________ 
Values of elemental analysis (as C.sub.29 H.sub.37 N.sub.2 O.sub.4 Cl) 
C H N Cl 
______________________________________ 
Found (%) 68.04 7.31 5.24 6.83 
Calcd. (%) 67.89 7.27 5.46 6.91 
______________________________________ 
NMR(.delta./CDCl.sub.3) 
##STR389## 
##STR390## 
##STR391## 
##STR392## 
##STR393## 
##STR394## 
##STR395## 
The same procedure as in Example 1 was repeated except that 6.2 parts of 
ethylene glycol was replaced with 15.5 parts of 3-bromo-1,2-propanediol, 
thereby obtaining 51.4 parts of 
3-bromo-1,2-bis[N-(4-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)carbamoylo 
xy]propane in the form of a colorless transparent liquid. 
______________________________________ 
Values of elemental analysis (as C.sub.29 H.sub.37 N.sub.2 O.sub.4 Br) 
C H N Br 
______________________________________ 
Found (%) 62.31 6.49 5.21 14.08 
Calcd. (%) 62.48 6.69 5.02 14.33 
______________________________________ 
NMR(.delta./CDCl.sub.3) 
##STR396## 
##STR397## 
##STR398## 
##STR399## 
##STR400## 
##STR401## 
##STR402## 
##STR403## 
The same procedure as in Example 2 was replaced except that 6.2 parts of 
ethylene glycol was replaced with 15.5 parts of 3-bromo-1,2-propanediol, 
thereby obtaining 52.3 parts of 
3-bromo-1,2-bis[N-(4-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)carbamoylo 
xy]propane in the form of a colorless transparent liquid. 
______________________________________ 
Values of elemental analysis (as C.sub.29 H.sub.37 N.sub.2 O.sub.4 Br) 
C H N Br 
______________________________________ 
Found (%) 62.29 6.81 5.13 14.15 
Calcd. (%) 62.48 6.69 5.02 14.33 
______________________________________ 
NMR(.delta./CDCl.sub.3) 
##STR404## 
##STR405## 
##STR406## 
##STR407## 
##STR408## 
##STR409## 
##STR410## 
The same procedure as in Example 1 was repeated except that 6.2 parts of 
ethylene glycol was replaced with 24.8 parts of 
2,3-dibromo-1,4-butanediol, thereby obtaining 59.8 parts of 
2,3-dibromo-1,4-bis[N-(3-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)carbam 
oyloxy]butane in the form of a colorless transparent liquid. 
______________________________________ 
Values of elemental analysis (as C.sub.30 H.sub.38 N.sub.2 O.sub.4 
Br.sub.2) 
C H N Br 
______________________________________ 
Found (%) 55.58 5.93 4.25 24.79 
Calcd. (%) 55.40 5.89 4.31 24.57 
______________________________________ 
NMR(.delta./CDCl.sub.3) 
##STR411## 
##STR412## 
##STR413## 
##STR414## 
##STR415## 
##STR416## 
##STR417## 
##STR418## 
The same procedure as in Example 2 was repeated except that 6.2 parts of 
ethylene glycol was replaced with 24.8 parts of 
2,3-dibromo-1,4-butanediol, thereby obtaining 57.6 parts of 
2,3-dibromo-1,4-bis[N-(4-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)carbam 
oyloxy]butane in the form of a colorless transparent liquid. 
______________________________________ 
Values of elemental analysis (as C.sub.30 H.sub.38 N.sub.2 O.sub.4 
Br.sub.2) 
C H N Br 
______________________________________ 
Found (%) 55.28 5.69 4.53 24.72 
Calcd. (%) 55.40 5.89 4.31 24.57 
______________________________________ 
NMR(.delta./CDCl.sub.3) 
##STR419## 
##STR420## 
##STR421## 
##STR422## 
##STR423## 
##STR424## 
##STR425## 
The same procedure as in Example 1 was repeated except that 6.2 parts of 
ethylene glycol was replaced with 26.2 parts of dibromoneopentyl glycol, 
thereby obtaining 62.1 parts of 
2,2-dibromomethyl-1,3-[N-(3-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)car 
bamoyloxy]propane in the form of a colorless transparent liquid. 
______________________________________ 
Values of elemental analysis (as C.sub.31 H.sub.40 N.sub.2 O.sub.4 
Br.sub.2) 
C H N Br 
______________________________________ 
Found (%) 55.93 6.14 4.18 24.00 
Calcd. (%) 56.04 6.07 4.22 24.05 
______________________________________ 
NMR(.delta./CDCl.sub.3) 
##STR426## 
##STR427## 
##STR428## 
##STR429## 
##STR430## 
##STR431## 
##STR432## 
The same procedure as in Example 2 was repeated except that 6.2 parts of 
ethylene glycol was replaced with 26.2 parts of dibromoneopentyl glycol, 
thereby obtaining 63.2 parts of 
2,2-dibromomethyl-1,3-bis[N-(4-isopropenyl-.alpha.,.alpha.-dimethylbenzyl) 
carbamoyloxy]propane in the form of a colorless transparent liquid. 
______________________________________ 
Values of elemental analysis (as C.sub.31 H.sub.40 N.sub.2 O.sub.4 
Br.sub.2) 
C H N Br 
______________________________________ 
Found (%) 56.21 6.03 4.39 24.32 
Calcd. (%) 56.04 6.07 4.22 24.05 
______________________________________ 
NMR(.delta./CDCl.sub.3) 
##STR433## 
##STR434## 
##STR435## 
##STR436## 
##STR437## 
##STR438## 
6.1 parts of glycerol, 30 parts of toluene, 40.3 parts of 
3-isopropenyl-.alpha.,.alpha.-dimethylbenzyl isocyanate and 0.2 part of 
dibutyltin dilaurate were mixed. The solution was then stirred for 1 hour, 
while the temperature of the solution was maintained at 90.degree. C., to 
carry out the reaction. After completion of the reaction, the reaction 
solution was concentrated. The resulting concentrate was then purified by 
chromatography, thereby obtaining 42.4 parts of 
1,2,3-tris[N-(3-isopropenyl-.alpha..alpha.-dimethylbenzyl)carbamoyloxy]pro 
pane. 
______________________________________ 
Values of elemental analysis (as C.sub.42 H.sub.53 N.sub.3 O.sub.6) 
C H N 
______________________________________ 
Found (%) 72.26 7.71 6.09 
Calcd. (%) 72.49 7.68 6.04 
______________________________________ 
NMR(.delta./CDCl.sub.3) 
##STR439## 
##STR440## 
##STR441## 
##STR442## 
##STR443## 
##STR444## 
##STR445## 
6.1 parts of glycerol, 30 parts of toluene, 26.8 parts of 
3-isopropenyl-.alpha.,.alpha.-dimethylbenzyl isocyanate and 0.2 part of 
dibutyltin dilaurate were mixed. The solution was then stirred for 1 hour, 
while the temperature of the solution was maintained at 60.degree. C. 
Afterward, 13.4 parts of 4-isopropenyl-.alpha.,.alpha.-dimethylbenzyl 
isocyanate was added thereto, and the solution was stirred for 1 hour, 
maintaining the temperature of the solution at 80.degree. C., to carry out 
reaction. After completion of the reaction, the reaction solution was 
concentrated. The resulting concentrate was then purified by 
chromatography, thereby obtaining 41.3 parts of 1,3-bis[N-(3-isopropenyl- 
, -dimethylbenzyl) carbamoyloxy]-2-[N-4-isopropenyl- , 
-dimethylbenzyl)carbamoyloxy]propane in the form of a colorless 
transparent liquid. 
______________________________________ 
Values of elemental analysis (as C.sub.42 H.sub.53 N.sub.3 O.sub.6) 
C H N 
______________________________________ 
Found (%) 72.31 7.74 6.17 
Calcd. (%) 72.49 7.68 6.04 
______________________________________ 
NMR(.delta./CDCl.sub.3) 
##STR446## 
##STR447## 
##STR448## 
##STR449## 
##STR450## 
##STR451## 
##STR452## 
EXAMPLE 49 The same procedure as in Example 47 was repeated except that 
.1 parts of ethylene glycol was replaced with 8.0 parts of 
trimethylolethane, thereby obtaining 44.5 parts of 1,1,1-tris[N-(3-isoprop 
enyl-.alpha.,.alpha.-dimethylbenzyl)carbamoyloxymethyl]ethane in the form 
of a colorless transparent liquid. 
______________________________________ 
Values of elemental analysis (as C.sub.44 H.sub.57 N.sub.3 O.sub.6) 
C H N 
______________________________________ 
Found (%) 72.87 7.98 5.75 
Calcd. (%) 73.00 7.94 5.80 
______________________________________ 
NMR(.delta./CDCl.sub.3) 
##STR453## 
##STR454## 
##STR455## 
##STR456## 
##STR457## 
##STR458## 
##STR459## 
##STR460## 
The same procedure as in Example 47 was repeated except that 6.1 parts of 
glycerol was replaced with 8.9 parts of trimethylolpropane, thereby 
obtaining 42.7 parts of 
2-ethyl-2-[N-(3-isopropenyl)-.alpha.,.alpha.-dimethylbenzyl)carbamoyloxyme 
thyl]-1,3-[N-(3-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)carbamoyloxy]pro 
pane in the form of a colorless transparent liquid. 
______________________________________ 
Values of elemental analysis (as C.sub.45 H.sub.59 N.sub.3 O.sub.6) 
C H N 
______________________________________ 
Found (%) 73.06 8.14 5.65 
Calcd. (%) 73.24 8.06 5.69 
______________________________________ 
NMR(.delta./CDCl.sub.3) 
##STR461## 
##STR462## 
##STR463## 
##STR464## 
##STR465## 
##STR466## 
##STR467## 
8.9 parts of trimethylolpropane, 30 parts of toluene, 13.4 parts of 
3-isopropenyl-.alpha.,.alpha.-dimethylbenzyl isocyanate, 26.8 parts of 
4-isopropenyl-.alpha.,.alpha.-dimethylbenzyl isocyanate and 0.2 part of 
dibutyltin dilaurate were mixed. The solution was then stirred for 1 hour, 
while the temperature of the solution was maintained at 80.degree. C., to 
carry out the reaction. After completion of the reaction, the reaction 
solution was concentrated. The resulting concentrate was then purified by 
chromatography, thereby obtaining 43.5 parts of 
2-ethyl-2-[N-(3-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)carbamoyloxymet 
hyl]-1,3-[N-(4-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)carbamoyloxy] 
propane in the form of a colorless transparent liquid. 
______________________________________ 
Values of elemental analysis (as C.sub.45 H.sub.59 N.sub.3 O.sub.6) 
C H N 
______________________________________ 
Found (%) 73.17 8.04 5.73 
Calcd. (%) 73.24 8.06 5.69 
______________________________________ 
NMR(.delta./CDCl.sub.3) 
##STR468## 
##STR469## 
##STR470## 
##STR471## 
##STR472## 
##STR473## 
The same procedure as in Example 47 was repeated except that 6.1 parts of 
glycerol was replaced with 7.1 parts of 1,2,4-butanetriol, thereby 
obtaining 41.8 parts of 
1,2,4-tris]N-(3-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)carbamoyloxy]bu 
tane in the form of a colorless transparent liquid. 
______________________________________ 
Values of elemental analysis (as C.sub.43 H.sub.55 N.sub.3 O.sub.6) 
C H N 
______________________________________ 
Found (%) 72.81 7.79 5.96 
Calcd. (%) 72.75 7.81 5.92 
______________________________________ 
NMR(.delta./CDCl.sub.3) 
##STR474## 
##STR475## 
##STR476## 
##STR477## 
##STR478## 
##STR479## 
##STR480## 
The same procedure as in Example 47 was repeated except that 6.1 parts of 
glycerol was replaced with 17.4 parts of 
1,3,5-tris(2-hydroxyethyl)cyanuric acid. The reaction solution was 
maintained under toluene reflux, thereby obtaining 49.9 parts of 
1,3,5-tris[2-(N-(3-isopropenyl-, -dimethylbenzyl)-carbamoyloxethyl)] 
isocyanurate in the form of a colorless transparent liquid. 
______________________________________ 
Values of elemental analysis (as C.sub.48 H.sub.60 N.sub.6 O.sub.9) 
C H N 
______________________________________ 
Found (%) 66.73 6.87 9.81 
Calcd. (%) 66.65 6.99 9.72 
______________________________________ 
NMR(.delta./CDCl.sub.3) 
##STR481## 
##STR482## 
##STR483## 
##STR484## 
##STR485## 
##STR486## 
##STR487## 
##STR488## 
##STR489## 
17.4 parts of 1,3,4-tris(2-hydroxyethyl)cyanuric acid, 30 parts of toluene, 
26.8 parts of 3-isopropenyl-.alpha.,.alpha.-methylbenzyl isocyanate, 13.4 
parts of 4-isopropenyl-.alpha.,.alpha.-dimethylbenzyl isocyanate and 0.2 
part of dibutyltin dilaurate were mixed. The solution was then stirred for 
1 hour under reflux, to carry out reaction. After completion of the 
reaction, the reaction solution was concentrated. The resulting 
concentrate was then purified by chromatography, thereby obtaining 51.4 
parts of 
1,3-bis[2-[N-(3-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)carbamoyloxyeth 
yl]]] isocyanurate in the form of a colorless transparent liquid. 
______________________________________ 
Values of elemental analysis (as C.sub.48 H.sub.60 N.sub.6 O.sub.9) 
C H N 
______________________________________ 
Found (%) 66.58 7.05 9.63 
Calcd. (%) 66.65 6.99 9.72 
______________________________________ 
NMR(.delta./CDCl.sub.3) 
##STR490## 
##STR491## 
##STR492## 
##STR493## 
##STR494## 
##STR495## 
##STR496## 
In the following examples, the high surface hardness transparent resin of 
201 parts of 3-isopropenyl-.alpha.,.alpha.-dimethylbenzylisocyanate was 
mixed with 1 part of dibutyltin dilaurate and 100 parts of methanol, and 
the mixture was then stirred for 30 minutes under methanol reflux in order 
to carry out the reaction. After completion of the reaction, methanol was 
distilled off, and the residue was then purified through a chromatography, 
thereby obtaining 198 parts of a colorless liquid monomer having the 
following structure: 
##STR497## 
To 116.7 parts of the monomer thus prepared added 70.6 parts of 
tris(acryloyloxyethyl) isocyanurate, and they were then mixed 
sufficiently. Afterward, 1.9 parts of benzoyl peroxide was added thereto, 
followed by mixing and defoaming. This solution was then poured into a 
mold prepared by interposing a 5-mm-thick polyvinyl chloride spacer 
between peripheral portions of two 5-mm-thick glass plates and then firmly 
fastening them together with a clamp, and polymerization was effected in a 
hot-air oven for polymerization by elevating the temperature therein rom 
70.degree. C. to 150.degree. C. over 1.5 hours. After cooling, a 
transparent resin plate having a smooth surface was released from the 
mold. 
EXAMPLE 56 
17.6 parts of pentaerythritol tetraacrylate and 0.3 part of benzoyl 
peroxide were added to 23.2 parts of 
1,2-bis[N-(3-isopropenyl-.alpha.,.alpha.,-dimethylbenzyl)carbamoyloxy]etha 
ne obtained by the same procedure as in Example 1, followed by sufficient 
mixing and defoaming. The resulting uniformed solution was then poured 
into a mold prepared by interposing a 5-mm-thick polyvinyl chloride spacer 
between peripheral portions of two 5-mm-thick glass plates and then firmly 
fastening them together with a clamp. Polymerization was then effected in 
a hot-air oven for polymerization by elevating the temperature therein 
from 70.degree. C. to 150.degree. C. over 1.5 hours. After cooling, a 
transparent resin plate having a smooth surface was released from the 
mold. 
EXAMPLE 57 
17.6 parts of pentaerythritol tetraacrylate and 0.3 part of benzoyl 
peroxide were added to 23.2 parts of 
1,2-bis[N-(4-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)carbamoyloxy]-etha 
ne obtained by the same procedure as in Example 2, followed by sufficient 
mixing and defoaming. The resulting uniformed solution was then poured 
into a mold prepared by interposing a 5-mm-thick polyvinyl chloride spacer 
between peripheral portions of two 5-mm-thick glass plates, and then 
firmly fastening them together with a clamp. Polymerization was then 
effected in a hot-air oven for polymerization by elevating the temperature 
therein from 70.degree. C. to 150.degree. C. over 1.5 hours. After 
cooling, a transparent resin plate having a smooth surface was released 
from the mold. 
EXAMPLE 58 
33.4 parts of trimethylolpropane trimethacrylate and 0.3 part of benzoyl 
peroxide were added to 25.4 parts of 
bis[2-(N-(3-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)carbamoyloxy)-ethyl 
] ether obtained by the same procedure as in Example 19, followed by 
sufficient mixing and defoaming. The resulting solution was then poured 
into a mold prepared by interposing a 5-mm-thick polyvinyl chloride spacer 
between peripheral portions of two 5-mm-thick glass plates and then firmly 
fastening them together with a clamp. Polymerization was then effected in 
a hot-air oven for polymerization by elevating the temperature therein 
from 70.degree. C. to 150.degree. C. over 1.5 hours. After cooling, a 
transparent resin plate having a smooth surface was released from the 
mold. 
EXAMPLE 59 
20.0 parts of ethyl acrylate and 0.3 part of benzoyl peroxide were added to 
29.9 parts of 
4,8-bis[N-(3-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)carbamoyloxymethyl 
]tricyclo[5,2,-1,0.sup.2,6 ]decane obtained by the same procedure as in 
Example 37, followed by sufficient mixing and defoaming. The resulting 
uniformed solution was then poured into a mold prepared by interposing a 
5-mm-thick polyvinyl chloride spacer between peripheral portions of two 
5-mm-thick glass plates and then firmly fastening them together with a 
clamp. Polymerization was then effected in a hot-air oven for 
polymerization by elevating the temperature therein from 70.degree. C. to 
150.degree. C. over 1.5 hours. After cooling, a transparent resin plate 
having a smooth surface was released from the mold. 
EXAMPLE 60 
26.4 parts of pentaerythritol tetraacrylate and 0.3 part of benzoyl 
peroxide were added to 31.7 parts of 
1,2,3-tris[N-(3-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)carbamoyloxy]pr 
opane obtained by the same procedure as in Example 47, followed by 
sufficient mixing and defoaming. The resulting uniformed solution was then 
poured into a mold prepared by interposing a 5-mm-thick polyvinyl chloride 
spacer between peripheral portions of two 5-mm-thick glass plates and then 
firmly fastening them together with a clamp. Polymerization was then 
effected in a hot-air oven for polymerization by elevating the temperature 
therein from 70.degree. C. to 150.degree. C. over 1.5 hours. After 
cooling, a transparent resin plate having a smooth surface was released 
from the mold. 
EXAMPLE 61 
42.3 parts of tris(acryloyloxyethyl)isocyanurate and 0.4 part of benzoyl 
peroxide were added to 43.3 parts of 
1,3,5-tris[2-(N-(3-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)carbamoyloxy 
ethyl]isocyanurate obtained by the same procedure as in Example 53, 
followed by sufficient mixing and defoaming. The resulting solution was 
then poured into a mold prepared by interposing a 5-mm-thick polyvinyl 
chloride spacer between peripheral portions of two 5-mm-thick glass plates 
and then firmly fastening them together with a clamp. 
Polymerization was then effected in a hot-air oven for polymerization by 
elevating the temperature therein from 70.degree. C. to 150.degree. C. 
over 1.5 hours. After cooling, a transparent resin plate having a smooth 
surface was released from the mold. 
EXAMPLE 62 
11.5 parts of glycerol and 0.5 part of dibutyltin dilaurate were added to 
100.6 parts of 3-isopropenyl-.alpha.,.alpha.-dimethylbenzyl isocyanate, 
and the mixture was then heated with stirring for 1 hour so that an 
internal temperature might be 80.degree. C. After cooling, 4.0 parts of 
methanol was added thereto, and heating was then carried out with stirring 
for 1 hour so that the internal temperature might be 55.degree. C., in 
order to obtain a mixture of two kinds of urethane compounds. To this 
mixture, 92.0 parts of pentaerythritol tetraacrylate was added, followed 
by mixing and defoaming. This solution was then poured into a mold 
prepared by interposing a 5-mm-thick polyvinyl chloride spacer between 
peripheral portions of two 5-mm-thick glass plates and then firmly 
fastening them together with a clamp. Polymerization was then effected in 
a hot-air oven for polymerization by elevating the temperature therein 
from 70.degree. C. to 150.degree. C. over 1.5 hours. After cooling, a 
transparent resin plate having a smooth surface was released from the 
mold. 
EXAMPLE 63 
11.6 parts of ethylene glycol and 0.1 part of dibutyltin dilaurate were 
added to 75.5 parts of 3-isopropenyl-.alpha.,.alpha.-dimethylbenzyl 
isocyanate, and the mixture was then heated with stirring for 1 hour so 
that an intenal temperature might be 70.degree. C. Afterward, 41.5 parts 
of N-(3-isopropenyl-.alpha.,.alpha.-dimethylbenzyl)-2-methacryloyloxy 
carbamate was added thereto. 
88.1 parts of pentaerythritol tetraacrylate and 1.0 part of benzoyl 
peroxide were added thereto, followed by sufficient mixing and defoaming. 
The solution was then poured into a mold prepared by interposing a 
5-mm-thick polyvinyl chloride spacer between peripheral portions of two 
5-mm-thick glass plates and then firmly fastening them together with a 
clamp. Polymerization was then effected in a hot-air oven for 
polymerization by elevating the temperature therein from 70.degree. C. to 
150.degree. C. over 1.5 hours. After cooling, a transparent resin plate 
having a smooth surface was released from the mold. 
For the transparent resin plates obtained in Examples 55 to 63, various 
physical properties were measured. The results are set forth in Table 1. 
In measuring these physical properties, the following procedures were 
employed: 
(1) Appearance: The appearance of each polymer plate was evaluated by 
observing the same by the naked eye. The polymer plates which were free 
from cracks and a rough surface were denoted by ".largecircle.", and the 
plates having such disadvantages were denoted by "X". 
(2) Surface Hardness This was measured by the use of a pencil scratching 
test machine for coating films under JIS-K-5401. 
(3) Heat Resistance: The resin plates were allowed to stand at 120.degree. 
C. for 4 hours in a hot-air drier Afterward, the resin plates were 
observed by the naked eye. The plates which were free from coloring and 
strain on the surfaces thereof were denoted by ".largecircle." and the 
plates having such drawbacks were denoted by "X". 
(4) Chemical Resistance: The polymer plates were immersed in isopropanol 
and toluene at room temperature for 24 hours. Afterward, they were 
scratched with an HB pencil The plates which were free from any traces 
were denoted by ".largecircle.", and the plates having some traces were 
denoted by "X". 
(5) Workability: The plates which could be abraded by a lens polisher for 
spectacle lens processing were denoted by ".largecircle.", and the plates 
which could not be done were denoted by "X". 
TABLE 1 
__________________________________________________________________________ 
Test Example 
Example 
Example 
Example 
Example 
Example 
Example 
Example 
Example 
Item 55 56 57 58 59 60 61 62 63 
__________________________________________________________________________ 
Appearance 
.largecircle. 
.largecircle. 
.largecircle. 
.largecircle. 
.largecircle. 
.largecircle. 
.largecircle. 
.largecircle. 
.largecircle. 
Surface 
5H 9H 9H 4H 4H 9H 6H 9H 9H 
Hardness or more 
or more or more or more 
or more 
Heat .largecircle. 
.largecircle. 
.largecircle. 
.largecircle. 
.largecircle. 
.largecircle. 
.largecircle. 
.largecircle. 
.largecircle. 
Resistance 
Chemical 
.largecircle. 
.largecircle. 
.largecircle. 
.largecircle. 
.largecircle. 
.largecircle. 
.largecircle. 
.largecircle. 
.largecircle. 
Resistance 
Workability 
.largecircle. 
.largecircle. 
.largecircle. 
.largecircle. 
.largecircle. 
.largecircle. 
.largecircle. 
.largecircle. 
.largecircle. 
__________________________________________________________________________ 
EXAMPLE 64 
0.1 part of benzoyl peroxide was added to 30 parts of a monomer mixture 
prepared by the same procedure as in Example 56, followed by sufficient 
mixing and defoaming. The mixture was then filtered through a filter 
having a pore diameter of 5 .mu.m under pressure, and then poured into a 
+2 diopter lens mold for diethylene glycol diallyl carbonate. Afterward, 
polymerization was effected by elevating the temperature of the mixture 
from 70.degree. C. to 140.degree. C. over 3 hours. After cooling, a 
transparent convex lens having a smooth surface was released from the 
mold. The pencil hardness on the surface of the convex lens was 9H or 
more, and a refractive index by the Abbe's refractometer was 1.54. 
EXAMPLE 65 
0.2 part of benzoyl peroxide was added to 20.0 parts of a monomer mixture 
prepared by the same procedure as in Example 56 followed by mixing and 
defoaming. 
The mixture was then applied onto a steel plate by the use of a coating bar 
so that a coating thickness might be 50 .mu.m. Afterward, the mixture was 
cured at a temperature of 140.degree. C. for 30 minutes, whereby a 
transparent coating film having a smooth surface was obtained on the steel 
plate. The pencil hardness of this coating film was 9H or more, and the 
results of a checker test (JIS K 5400) were good. In addition, heat 
resistance was also good (the specimens were allowed to stand at 
120.degree. C. for 10 hours in a hot-air drier, and those which were free 
from any problems were evaluated to be good). 
COMATIVE EXAMPLE 1 
3.0 parts of benzoyl peroxide was added to 100 parts of diethylene glycol 
diallyl carbonate, followed by mixing and defoaming. This solution was 
then poured into a mold prepared by interposing a 5-mm-thick polyvinyl 
chloride spacer between peripheral portions of two 5-mm-thick glass plates 
and then firmly fastening them together with a clamp, and it was tried 
that polymerization was effected in a hot-air oven for polymerization by 
elevating the temperature therein from 70.degree. C. to 120.degree. C. 
over 3 hours. However, when the temperature reached about 70.degree. C. in 
the course of the polymerization, the polymerization advanced vigorously, 
so that the polymer was peeled from the glass mold and was colored yellow. 
Only when the polymerization was carried out by elevating the temperature 
from 50.degree. C. to 120.degree. C. over 10 hours, a resin plate could be 
obtained without peeling from the mold, but the pencil hardness of the 
obtained resin was 3 H. 
COMATIVE EXAMPLE 2 
18.8 parts of m-xylylene diisocyanate was added to 20.0 parts of methyl 
methacrylate, and 0.5 part of dibutyltin laurate was further added 
thereto. 26.0 parts of hydroxyethyl methacrylate was slowly added thereto, 
while heating PG,147 was carried out so that an internal temperature might 
be 60 .degree. C., thereby obtaining a viscous methyl methacrylate mixture 
of an urethane compound in which the infrared spectrum absorption based on 
an isocyanate group was scarcely seen. 0.3 part of benzoyl peroxide was 
further added thereto, followed mixing and defoaming, and the solution was 
then poured into a mold prepared by interposing a 5-mm-thick polyvinyl 
chloride spacer between peripheral portions of two 5-mm-thick glass plates 
and then firmly fastening them together with a clamp, and it was tried 
that polymerization was effected in a hot-air oven for polymerization by 
elevating the temperature therein from 45.degree. C. to 120.degree. C. 
over 3 hours. However, when the temperature reached about 65.degree. C. in 
the course of the polymerization, the polymerization advanced vigorously, 
so that the polymer was peeled from the glass mold. 
COMATIVE EXAMPLE 3 
0.5 part of benzoyl peroxide was added to 50 parts of trimethylolpropane 
triacrylate, followed mixing and defoaming. This solution was then poured 
into a mold prepared by interposing a 5-mm-thick polyvinyl chloride spacer 
between peripheral portions of two 5-mm-thick glass plates and then firmly 
fastening them together with a clamp, and it was tried that polymerization 
was effected in a hot-air oven for polymerization by elevating the 
temperature therein from 60.degree. C. to 140.degree. C. over 3 hours. 
However, at an early stage in the course of the polymerization, the 
polymerization advanced vigorously, so that the polymer was peeled from 
the glass mold. 
Other embodiments of the invention will be apparent to those skilled in the 
art from consideration of the specification and practice of the invention 
disclosed herein. It is intended that the specification and examples be 
considered as exemplary only, with the true scope and spirit of the 
invention being indicated by the following claims.