CA1159194A - Terpolymer with a high refractive index - Google Patents
Terpolymer with a high refractive indexInfo
- Publication number
- CA1159194A CA1159194A CA000388414A CA388414A CA1159194A CA 1159194 A CA1159194 A CA 1159194A CA 000388414 A CA000388414 A CA 000388414A CA 388414 A CA388414 A CA 388414A CA 1159194 A CA1159194 A CA 1159194A
- Authority
- CA
- Canada
- Prior art keywords
- lens
- high refractive
- refractive index
- terpolymer
- triallylisocyanurate
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 229920001897 terpolymer Polymers 0.000 title claims abstract description 7
- AOJOEFVRHOZDFN-UHFFFAOYSA-N benzyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC1=CC=CC=C1 AOJOEFVRHOZDFN-UHFFFAOYSA-N 0.000 claims abstract description 12
- KOMNUTZXSVSERR-UHFFFAOYSA-N 1,3,5-tris(prop-2-enyl)-1,3,5-triazinane-2,4,6-trione Chemical compound C=CCN1C(=O)N(CC=C)C(=O)N(CC=C)C1=O KOMNUTZXSVSERR-UHFFFAOYSA-N 0.000 claims abstract description 10
- SYFOAKAXGNMQAX-UHFFFAOYSA-N bis(prop-2-enyl) carbonate;2-(2-hydroxyethoxy)ethanol Chemical compound OCCOCCO.C=CCOC(=O)OCC=C SYFOAKAXGNMQAX-UHFFFAOYSA-N 0.000 claims abstract description 4
- 239000000203 mixture Substances 0.000 claims description 2
- 230000000379 polymerizing effect Effects 0.000 claims 1
- 239000011521 glass Substances 0.000 abstract description 9
- 239000000178 monomer Substances 0.000 abstract description 5
- 238000002834 transmittance Methods 0.000 abstract description 3
- 230000000704 physical effect Effects 0.000 abstract description 2
- 238000006116 polymerization reaction Methods 0.000 abstract description 2
- JHQVCQDWGSXTFE-UHFFFAOYSA-N 2-(2-prop-2-enoxycarbonyloxyethoxy)ethyl prop-2-enyl carbonate Chemical compound C=CCOC(=O)OCCOCCOC(=O)OCC=C JHQVCQDWGSXTFE-UHFFFAOYSA-N 0.000 description 10
- 238000007334 copolymerization reaction Methods 0.000 description 2
- 239000011259 mixed solution Substances 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 238000007689 inspection Methods 0.000 description 1
- 230000001678 irradiating effect Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
Landscapes
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Abstract
TITLE OF THE INVENTION
A TERPOLYMER WITH A HIGH REFRACTIVE INDEX
ABSTRACT OF THE DISCLOSURE
A high refractive lens of a terpolymer produced by the polymerization of ternary monomers comprising diethylene glycol bisallyl carbonate, triallylisocyanurate, and benzyl methacrylate. This lens is considerably improved in its physical properties necessary for lens such as superficial hardness, transmittance, and adhesion strength of glass film coated on the surface, as well as having a high refractive index.
A TERPOLYMER WITH A HIGH REFRACTIVE INDEX
ABSTRACT OF THE DISCLOSURE
A high refractive lens of a terpolymer produced by the polymerization of ternary monomers comprising diethylene glycol bisallyl carbonate, triallylisocyanurate, and benzyl methacrylate. This lens is considerably improved in its physical properties necessary for lens such as superficial hardness, transmittance, and adhesion strength of glass film coated on the surface, as well as having a high refractive index.
Description
~ 159i~4 BACKGROUND OF T~IE INVENTION
1. Field of the Invention lhis invention relates to a terpolymer with a high refractive index and the plastic lenses made of the terpolymer.
1. Field of the Invention lhis invention relates to a terpolymer with a high refractive index and the plastic lenses made of the terpolymer.
2. Description of the Prior Art Recently lenses of organic glass have been widely used instead of lenses of inorganic glass, because organic glass is superior to inorganic glass in its lightness, safety due to its high impact resistance, workability, dyeability, etc. For example, lenses made of diethylene glycol bisallyl carbonate (hereinafter referred to CR39) have already been used widely. But, lenses of CR39 have such a disadvantage that the lenses must be thicker than those of inorganic glass, because of their relatively low refractive index such as 1.499. There is known a method for overcoming the disadvantage comprising copolymerizing CR39 with benzyl methacrylate so as to increase the refractive index.
However, lenses obtained by the copolymerization are inferior to lenses of CR39 in their superficial hardness, so that the lenses must be more carefully handled.
We have now found that copolymerization of ternary monomers consisting of CR39, benzyl methacrylate, and triallylisocyanurate enables to produce lens with a high refractive index and a high superficial hardness.
An object of this invention is to provide a plastic 1 159~'~4 lens with a hi~h refractive index and a high superficial hardness.
SUMMARY OF rHE INV~NTION
This invention relates to a terpolymer produced by the polymerization of ternary monomers comprising diethylene glycol bisallyl carbonate, triallylisocyanurate and benzyl methacrylate.
DETAILED DESCRIPTION OF THE PREF~RRED EMBODIMENTS
In this invention, CR39 is preferabiy used in the range of 40 wt.% to 80 wt.~. Benzyl methacrylate is preferably used in the range of 10 wt.% to 30 wt.%.
Triallylisocyanurate is preferably used in the range o~
10 wt.% to 30 wt.%. And, it is preferable that the amount of benzylmethacrylate is not larger than that of triallyl-isocyanurate. The more the amount of benzylmethacrylate than that of triallylisocyanurate, the lower the transparency of the lens produced therefrom. On the contrary, when the amount of triallylisocyanurate is extremely larger than that of benzyl methacrylate, the lens thereof is liable to be easily cracked.
The lens of this invention can be prepared by pouring the mixed solution consisting of CR39, benzyl methacrylate 9 triallylisocyanurate, and initiator into a mold made of two ~ 159194 plates of glass mold and a plastic gasket, and then curing the resulting one by means of heating it or irradiating it with ultraviolet ray.
The high refractive lens of this invention is mOTe improved than the lens obtained by copolymerizing CR39 with a methacrylate such as benzyl methacrylate in its superficial hardness, transmittance, and adhesion of coating material.
Namely, the lens of this invention is the one whose refractive index and superficial hardness are increased with keeping the same excellent physical properties as are inherent in the lens of CR39. Such remarkable effect seems to have never been performed in the copolymer of binary monomers.
This invention will be more clearly understood with reference to the following Examples.
Example 1 A mixed solution consisting of 60 wt. parts of CR39, 20 wt. parts of benzylmethacrylate, 20 wt. parts of triallyl-isocyanurate, and 5 wt. parts of diisopropylperoxydicarbona~e was poured into a mold made of two plates of glass mold and a plastic gasket. The one was heated to elevate the temperature from 40C to 90C in 24 hours. After curing, the lens was taken out of the mold, and heat-treated at 120C for one hour. The lens obtained possessed 1.523 of refractive index, 92 % of transmittance (550 nm), 3H of pencil hardness, and an impact resistance which passed 1 1591~4 inspection of FDA Standard. Adhesion of a glass film coated on the lens surface by vacuum evaporation method stood the cross cut test and alkali-resisting test.
In example 2 and 3, and comparative example 1 - 5, lenses were prepared in the same manner as in Example 1, except that the monomer composition in Table 1 were used.
Table 1 shows the result.
llS~lg~
~ ---- --~
I ~4~
~ ~ rol ~ ~
~: h O `d ~<J O O O
~o ~
.Y ~Y ~
~ U~ ~ ~
a~ u, ~ ~ ~4 ~1 'U~ ::CU U :~ :r: ~
~ ~ ~ l ~ o ~ o ~ ~ ~
~~ ~:~::~ C) C~ ~ h h ~1 __ ~ _ ~ _ . ~d td ~ v~
u O ~ cn a~ a~ ~7 ~ ~ _~ ~ ~ 3 P. ~ ~ _~ ~ ~ ~ ~ ~1t~7 ~ t~ t~
C~ ~ L~ U~ U~ U~ ~ 1 ~ O
. . . ~ . ~a. . .
~1 ~1 ~ ~1 ~_~ _~_~ ~ ~ _0 ~ h h v~ ~ ~ ~ ~
_~ O O ,1 Vl ~1 ~ ~ O
~ ~1 ~H _ ~ h ~
_I U U~
E- ~ V) u~ ~ ~ o ~ _~ ~ ~1 ~ O ~ ~ ~ _~
.,~ o\ o~ o- ~ a~ ~o~ a~ o~ o 1:: ~ ~ ~1 ~ ~1 ~
h O O O ~ h ~ ~,C,C
~ __ _ _ ~ S O
o~ U o O O o o O o o -~ P'~ ......
~ c~ r~ ,1 ~ ~`1 ~1 r~7 ~ r~J ~ ~ h OG X
~ ~ ~U~
Q r-l ~ h ~ ~0 ~ O 0 0 O
~ O r~ ~ D 5 O ~O o o o o o o o U ~ ~:: ~ O
t~ ~ ~ ~1 ~ _1 ~) ~
~3 ~ bl~ Uo _ ~
v~
~ h ~: o ~_t~ n m ~Ooo ~ ~ ~
However, lenses obtained by the copolymerization are inferior to lenses of CR39 in their superficial hardness, so that the lenses must be more carefully handled.
We have now found that copolymerization of ternary monomers consisting of CR39, benzyl methacrylate, and triallylisocyanurate enables to produce lens with a high refractive index and a high superficial hardness.
An object of this invention is to provide a plastic 1 159~'~4 lens with a hi~h refractive index and a high superficial hardness.
SUMMARY OF rHE INV~NTION
This invention relates to a terpolymer produced by the polymerization of ternary monomers comprising diethylene glycol bisallyl carbonate, triallylisocyanurate and benzyl methacrylate.
DETAILED DESCRIPTION OF THE PREF~RRED EMBODIMENTS
In this invention, CR39 is preferabiy used in the range of 40 wt.% to 80 wt.~. Benzyl methacrylate is preferably used in the range of 10 wt.% to 30 wt.%.
Triallylisocyanurate is preferably used in the range o~
10 wt.% to 30 wt.%. And, it is preferable that the amount of benzylmethacrylate is not larger than that of triallyl-isocyanurate. The more the amount of benzylmethacrylate than that of triallylisocyanurate, the lower the transparency of the lens produced therefrom. On the contrary, when the amount of triallylisocyanurate is extremely larger than that of benzyl methacrylate, the lens thereof is liable to be easily cracked.
The lens of this invention can be prepared by pouring the mixed solution consisting of CR39, benzyl methacrylate 9 triallylisocyanurate, and initiator into a mold made of two ~ 159194 plates of glass mold and a plastic gasket, and then curing the resulting one by means of heating it or irradiating it with ultraviolet ray.
The high refractive lens of this invention is mOTe improved than the lens obtained by copolymerizing CR39 with a methacrylate such as benzyl methacrylate in its superficial hardness, transmittance, and adhesion of coating material.
Namely, the lens of this invention is the one whose refractive index and superficial hardness are increased with keeping the same excellent physical properties as are inherent in the lens of CR39. Such remarkable effect seems to have never been performed in the copolymer of binary monomers.
This invention will be more clearly understood with reference to the following Examples.
Example 1 A mixed solution consisting of 60 wt. parts of CR39, 20 wt. parts of benzylmethacrylate, 20 wt. parts of triallyl-isocyanurate, and 5 wt. parts of diisopropylperoxydicarbona~e was poured into a mold made of two plates of glass mold and a plastic gasket. The one was heated to elevate the temperature from 40C to 90C in 24 hours. After curing, the lens was taken out of the mold, and heat-treated at 120C for one hour. The lens obtained possessed 1.523 of refractive index, 92 % of transmittance (550 nm), 3H of pencil hardness, and an impact resistance which passed 1 1591~4 inspection of FDA Standard. Adhesion of a glass film coated on the lens surface by vacuum evaporation method stood the cross cut test and alkali-resisting test.
In example 2 and 3, and comparative example 1 - 5, lenses were prepared in the same manner as in Example 1, except that the monomer composition in Table 1 were used.
Table 1 shows the result.
llS~lg~
~ ---- --~
I ~4~
~ ~ rol ~ ~
~: h O `d ~<J O O O
~o ~
.Y ~Y ~
~ U~ ~ ~
a~ u, ~ ~ ~4 ~1 'U~ ::CU U :~ :r: ~
~ ~ ~ l ~ o ~ o ~ ~ ~
~~ ~:~::~ C) C~ ~ h h ~1 __ ~ _ ~ _ . ~d td ~ v~
u O ~ cn a~ a~ ~7 ~ ~ _~ ~ ~ 3 P. ~ ~ _~ ~ ~ ~ ~ ~1t~7 ~ t~ t~
C~ ~ L~ U~ U~ U~ ~ 1 ~ O
. . . ~ . ~a. . .
~1 ~1 ~ ~1 ~_~ _~_~ ~ ~ _0 ~ h h v~ ~ ~ ~ ~
_~ O O ,1 Vl ~1 ~ ~ O
~ ~1 ~H _ ~ h ~
_I U U~
E- ~ V) u~ ~ ~ o ~ _~ ~ ~1 ~ O ~ ~ ~ _~
.,~ o\ o~ o- ~ a~ ~o~ a~ o~ o 1:: ~ ~ ~1 ~ ~1 ~
h O O O ~ h ~ ~,C,C
~ __ _ _ ~ S O
o~ U o O O o o O o o -~ P'~ ......
~ c~ r~ ,1 ~ ~`1 ~1 r~7 ~ r~J ~ ~ h OG X
~ ~ ~U~
Q r-l ~ h ~ ~0 ~ O 0 0 O
~ O r~ ~ D 5 O ~O o o o o o o o U ~ ~:: ~ O
t~ ~ ~ ~1 ~ _1 ~) ~
~3 ~ bl~ Uo _ ~
v~
~ h ~: o ~_t~ n m ~Ooo ~ ~ ~
3 U ~1 C~ h _ _ _ . .,~
_~~ ~ ~ ~~1 ~ ~ ~ ~ ~
.,~ 00 X Q~ .... -- E~
a- ~ U
. _ : :: ~t : _ ~: ¢ h ~ O
O X U
U ___ _ _
_~~ ~ ~ ~~1 ~ ~ ~ ~ ~
.,~ 00 X Q~ .... -- E~
a- ~ U
. _ : :: ~t : _ ~: ¢ h ~ O
O X U
U ___ _ _
Claims
PROPERTY OR PRIVILEGE IS CLAIMED ARE DEFINED AS FOLLOWS:
1. A high refractive lens formed of a terpolymer produced by polymerizing a mixture comprising by weight 40 to 80% of diethylene glycol bisallyl carbonate, 10 to 30% of triallylisocyanurate and 10 to 30% of benzyl methacrylate.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CA000388414A CA1159194A (en) | 1981-10-21 | 1981-10-21 | Terpolymer with a high refractive index |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CA000388414A CA1159194A (en) | 1981-10-21 | 1981-10-21 | Terpolymer with a high refractive index |
Publications (1)
Publication Number | Publication Date |
---|---|
CA1159194A true CA1159194A (en) | 1983-12-20 |
Family
ID=4121220
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CA000388414A Expired CA1159194A (en) | 1981-10-21 | 1981-10-21 | Terpolymer with a high refractive index |
Country Status (1)
Country | Link |
---|---|
CA (1) | CA1159194A (en) |
-
1981
- 1981-10-21 CA CA000388414A patent/CA1159194A/en not_active Expired
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
MKEX | Expiry | ||
MKEX | Expiry |
Effective date: 20001220 |