OPTICAL MATERIAL, COMPOSITION FOR OPTICAL MATERIAL; AND USE THEREOF
5 TECHNICAL FIELD
[0001]
The present invention relates to an optical material, a
composition for an optical material, and use thereof.
10 BACKGROUND ART
[0002]
In the related art, a fact that exposure to ultraviolet rays
exerts a negative influence on the eye is regarded as an issue.
Furthermore, in recent years, a fact that blue light, Hhich is included
15 in natural light or in light emitted from liquid crystal displays
of office machines, displays of portable devices such as smartphones
or cellular phones, and the like, exerts an influence on the eye and
makes the eye feel fatigue or pain has become an issue. Therefore,
it is required to reduce exposure of the eye to ultraviolet rays and
20 blue light having a relatively short v1avelength of about 420 nm.
[0003]
Non-Patent Document 1 describes the influence of
short-Havelength blue light of about 420 nm on the eye.
In this document, damage of retinal neuronal cells (rat R28
25 retinal neuronal culture cells) irradiated with blue LED lights
having different peak wavelengths of 411 nm and 470 nm was verified.
As a result, it was found that while irradiation (4.5 W/m2
) of blue
l
2
light having a peak wavelength at 411 nm caused death of the retinal
neuronal cells within 24 hours, blue light having a peak wavelength
at 470 nm caused no change in the cells even if the cells were
irradiated with this light at the same dose. This result shmvs that
5 in order to prevent eye injury, it is important to inhibit exposure
of the eye to light having a 1vavelength of 400 mn to 420 nrn.
[0004]
Moreover, it is considered that if irradiated loJith blue light
for a long time, the eye may suffer from fatigue or stress, and this
10 may lead to age-related macular degeneration.
15
RELATED DOCUMENT
PATENT DOCUMENT
[0005]
[Patent Document 1] Japanese Unexamined Patent Publication No.
10-186291
[Patent Document 2] Japanese Unexamined Patent Publication No.
11-218602
[Patent Document 3] Japanese Unexamined Patent Publication No.
20 11-295502
[Patent Document 4] Japanese Unexamined Patent Publication No.
2000-147201
[Patent Document 5] Pamphlet of International Publication No.
W02006/087880
25 NON-PATENT DOCUMENT
[0006]
[Non-Patent Document 1] The European journal of neuroscience
l
5
10
vol. 34, Iss. 4, 548-558, (2011)
DISCLOSURE OF THE INVENTION
[0007]
3
Patent Document 1 discloses a technique for suppressing an
average light transmittance within a range of equal to or greater
than 300 nm and equal to or less than 400 nm by adding an ultraviolet
absorber.
[0008]
Patent Document 2 discloses a technique that uses at least two
kinds of ultraviolet absorber differing from each other in terms of
maximum absorption wavelength. Patent Document 3 discloses a
technique regarding a plastic lens that does not undergo yellowing,
change in refractive index, and the like even when an ultraviolet
15 absorber is added thereto and does not experience decrease in
mechanical strength. Ho1vever, the techniques disclosed in the
documents merely relate to spectral transmittance at 400 nm, and the
documents do not include a disclosure regarding light transmittance
at 420 nm and 440 nm.
20 [0009]
Patent Document 4 discloses a technique in which a benzotriazole
derivative is added as an ultraviolet absorber, and discloses an
ultraviolet transmittance in a plastic lens having a thickness of
1.1 mm at a wavelength equal to or iess than 400 nm.
25 [0010]
Herein, when an ultraviolet absorber is used to cut a
low-wavelength region of a 1vavelength of 400 nm to 420 nm, depending
4
on the type of the ultraviolet absorber, the resin turns yellow in
some cases, or alternatively, the ultraviolet absorber is
precipitated without being completely dissolved in a composition for
an optical material and becomes opaque in some cases.
5 [0011]
In the technique disclosed in Patent Document 5, fine iron oxide
particles are added to a composition, and consequentially, a molded
product is colored in some cases. Therefore, in the field of
spectacle lenses or the like that require transparency, the technique
10 causes a problem in external appearance. Furthermore, a
polycarbonate resin, which has been used as a transparent
thermoplastic resin, needs to be further improved in terms of optical
properties such as the refractive index or Abbe number.
[0012]
15 The present invention includes the following.
[1] An optical material that contains one or more kinds of
ultraviolet absorber (a) having a maximum absorption peak within a
range of equal to or greater than 350 nm and equal to or less than
370 nm, in which a light transmittance of the optical material having
20 a thickness of 2 mrn satisfies the follmving characteristics (1) to
( 3) '
( 1) a light.transmittance at a wavelength of 410 nm is equal
to or less than 10%,
( 2) a light transmittance at a \vavelength of 420 nrn is equal
25 to or less than 70%, and
( 3) a light transmittance at a wavelength of 440 nm is equal
to or greater than 80%.
5
[2] The optical material described in [1], in which the
ultraviolet absorber (a) is selected from benzotriazole-based
compounds.
[3] The optical material described in [1] or [2], in which the
5 ultraviolet absorber (a) is
2-(2-hydroxy-3-t-butyl-5-methylphenyl)-chlorobenzotriazole.
[4] The optical material described in any one of [1] to [3],
that contains at least one kind selected from polyurethane,
polythiourethane, polysulfide, polycarbonate, poly(meth)acrylate,
10 and polyolefin.
[5] The optical material described in any one of [1] to [4],
including a lens substrate, and a film layer and a coating layer that
are optionally laminated over the lens substrate.
[6] The optical material described in any one of [1] to [5],
15 including the lens substrate, and the film layer and the coating layer
that are optionally laminated over the lens substrate, in which the
ultraviolet absorber (a) is contained in at least one of the lens
substrate, the film layer, and the coating layer.
[7] The optical material described in any one of [1] to [6] that
20 is obtained from a composition for an optical material containing
one or more kinds of ultraviolet absorber (a) having a maximum
absorption peak wi"th"in a range of equal to or greater than 350 nm
and equal to or less than 370 nm and a resin for an optical material
(b) or a polymerizable compound (c), in which the amount of the
25 ultraviolet absorber (a) contained in the composition is 0.3% by
weight to 2% by Height >vi th respect to the total weight of the resin
for an optical material (b) or the polymerizable compound (c) .
6
[8] The optical material described in [7], in which the
ultraviolet absorber (a) is one or more kinds of compound selected
from benzotriazole-based compounds.
[9] The optical material described in [7] or [8], in 1-1hich the
5 resin for an optical material (b) is at least one kind selected from
polycarbonate, poly(meth)acrylate, and polyolefin.
[10] The optical material described in [7] or [8], in which the
polymerizable compound (c) is a combination of a polyisocyanate
compound and a polyol compound, a combination of a polyisocyanate
10 compound and a polythiol compound, a polyepithio compound and/or a
poiythietane compound, or a combination of a polyepithio compound
and a polythiol compound.
[11] A plastic spectacle lens comprised of the optical material
described in any one of [1] to [10].
15 [12] A composition for an optical material including one or more
kinds of ultraviolet absorber (a) having a maximum absorption peak
within a range of equal to or greater than 350 nm and equal to or
less than 370 nm, and a resin for an optical material (b) or a
polymerizable compound (c) , in 1vhich the amount of the ultraviolet
20 absorber (a) contained in the composition is 0. 3% by 1-1eight to 2%
by 1-1eight 1-1ith respect to the total weight of the resin for an optical
material (b), or the polymerizable compound (c) .
[13] The composition for an optical material described in [12],
in which the ultraviolet absorber (a) is one or more kinds of compound
25 selected from benzotriazole-based compounds.
[14] The composition for an optical material described in [12]
or [13], in which the resin for an optical material (b) is at least
--- ----- ----------------
7
one kind selected from polycarbonate, poly(meth)acrylate, and
polyolefin.
[15] The composition for an optical material described in [12]
or [13], in which the polymerizable compound (c) is a combination
5 of a polyisocyanate compound and a polyol compound, a combination
of a polyisocyanate compound and a polythiol compound, a polyepithio
compound and/or a polythietane compound, or a combination of a
polyepithio compound and a polythiol compound.
[16] A manufacturing method of an optical material, including
10 a step of obtaining the composition for an optical material described
in any one of [12] to [15] by mixing the ultraviolet absorber (a)
with the resin for an optical material (b) or the polymerizable
compound (c), and a step of curing the composition for an optical
material.
15 [17] A molded product obtained by curing the composition for
an optical material described in any one of [12] to [15].
[18] An optical material comprised of the molded product
described in [17].
[19] A plastic spectacle lens including a lens substrate
20 comprised of the molded product described in [17].
[20] A film obtained from the molded product described in [17].
[21] A coating material comprised of the composition for an
optical material described in any one of [12] to [15].
[22] A plastic spectacle lens including a layer comprised of
25 the film described in [20] over at least one surface of a lens
substrate.
[23] A plastic spectacle lens including lens substrate layers
8
over both surfaces of the film described in [20].
[24] A plastic spectacle lens including a coating layer, which
is obtained by curing the coating material described in [21], over
at least one surface of a lens substrate.
5 [0013]
According to the present invention, it is possible to provide
an optical material Hhich exerts a strong effect of blocking from
harmful ultraviolet rays to blue light of about 420 nm and has an
excellent external appearance that is colorless and transparent. The
10 optical material of the present invention has excellent optical
characteristics such as a high refractive index and a high Abbe number,
has an excellent external appearance that is colorless and
transparent, and can prevent injury including eye fatigue and stress
by reducing influence of harmful light on the eye. Therefore, the
15 optical material can be suitably used particularly as a plastic
spectacle lens.
20
25
BRIEF DESCRIPTION OF THE DRAWINGS
[ 00 14]
FIG. 1 is a chart showing ultraviolet-visible light spectra of
lenses prepared in Examples 1 and 3 and Com~arative example 2.
FIG. 2 is .. a chart showing ultraviolet -visible light spectra of
ultraviolet absorbers, which are used in examples and comparative
examples, in a chloroform solution.
DESCRIPTION OF EMBODIMENTS
[0015]
l
~~------------------------------------------
9
Hereinafter, embodiments of the present invention will be
specifically described.
The optical material of the present invention contains an
ultraviolet absorber (a) having a maximum absorption wavelength of
5 equal to or greater than 350 nm and equal to or less than 370 nm,
and a light transmittance of the optical material having a thickness
of 2 mm satisfies the following characteristics (1) to (3) .
10
15
(1) A light transmittance at a wavelength of 410 nm is equal
to or less than 10%.
(2) A light transmittance at a wavelength of 420 nm is equal
to or less than 70%.
(3) A light transmittance at a wavelength of 440 nm is equal
to or greater than 80%.
[ 0016]
The present inventors found that by using a specific ultraviolet
absorber having a maximum absorption 1-1avelength 1-1ithin a range of
equal to or greater than 350 nm and equal to or less than 370 nm,
an optical material that selectively absorbs light in a
low-wavelength region of 400 nm to 420 nm can be obtained, and the
20 optical material has excellent optical characteristics such as a high
refractive index and a high Abbe number and has an excellent external
appearance that is. colorless and transparent. Based on these
findings, they completed the present invention.
That is, because the optical material contains the ultraviolet
25 absorber (a) and has a light transmittance that is within the
aforementioned range at a specific wavelength, the optical material
has an excellent external appearance including transparency, has
10
excellent optical characteristics such as a high refractive index
and a high Abbe number, is prevented from becoming colored, and can
prevent injury including eye fatigue and stress. Furthermore,
because the optical material has a light transmittance of equal to
5 or greater than 80% at a wavelength of 440 nm, it can be obtained
in the form of a colorless and transparent optical material having
excellent an external appearance.
[0017]
Hereinafter, embodiments of the present invention will be
10 specifically described.
In a first embodiment, an embodiment will be described in which
an optical material is prepared by using a composition for an optical
material containing the ultraviolet absorber (a). In a second
embodiment, an embodiment will be described in which a molded product
15 is prepared by using a composition for an optical material not
containing the ultraviolet absorber (a), and an optical material is
prepared by adding the ultraviolet absorber (a) to the molded product
by a predetermined method.
[0018]
20 [First embodiment]
A composition for an optical material of the present embodiment
contains one or more kinds of ultraviolet absorber (a) having a maximum
absorption peak within a range of equal to or greater than 350 nm
and equal to or less than 370 nm, and a resin for an optical material
25 (b) or a polymerizable compound (resin monomer) (c). Hereinafter,
each of the components 1-1ill be described in detail.
[0019]
---------------------------
11
[Ultraviolet absorber (a)]
The ultraviolet absorber (a). used in the present embodiment is
not particularly limited as long as it has a maximum absorption
Navelength 1vithin a range of equal to or greater than 350 nm and equal
5 to or less than 370 nm 1vhen being dissolved in a chloroform solution.
As the ultraviolet absorber (a), benzotriazole-based compounds
are preferably used.
In the present embodiment, as the ultraviolet absorber (a), one
or more kinds of such ultraviolet absorbers are preferably used.
10 Furthermore, the composition for an optical material may contain tl'lo
or more different kinds of the ultraviolet absorber (a). Herein,
any of ultraviolet absorbers constituting the ultraviolet absorber
(a) has a maximum absorption peak within a range of equal to or greater
than 350 nm and equal to or less than 370 nm.
15 [0020]
The ultraviolet absorber (a) can be contained in any of a lens
substrate, a film layer, and a coating layer which will be described
later. As the film layer or the coating layer, it is possible to
use materials having polarization properties or materials having
20 photochrornic properties.
Preferable examples of the ultraviolet absorber (a) used in the
present embodiment include
2-(2-hydroxy-3-t-butyl-5-methyphenyl)-chlorobenzotriazole.
Examples of commercially available products thereof include
25 TINUVIN326 manufactured by BASF Corporation, SEESEORB703
manufactured by SHIPRO KASEI KAISHA, LTD., Viosorb550 manufactured
by KYODO CHEMICAL CO., LTD., KEMISORB73 manufactured by CHEMIPRO
l
KASEI, and the like.
[0021]
12
[Resin for optical material (b) or polymerizable compound (c)]
In the present embodiment, the composition ·for an optical
5 material contains the resin for an optical material (b) or the
polymerizable compound (c) . The resin for an optical material and
a resin obtained from the polymerizable compound (hereinafter, all
of the resins will be simply referred to as a "resin" in some cases)
are preferably transparent resins.
10 [0022]
(Resin for optical material (b))
As the resin for an optical material (b), polycarbonate,
poly(meth)acrylate, polyolefin, cyclic polyolefin, polyallyl,
polyurethane urea, a polyene-polythiol polymer, a ring-opening
15 metathesis polymer, polyester, and an epoxy resin can be preferably
used. These are materials (transparent resins) having a high degree
of transparency, and can be suitably used for optical materials. At
least one kind selected from polycarbonate, poly (meth) acrylate, and
polyolefin can be more preferably used as the materials. These are
20 materials having a high degree of transparency, and can be suitably
used for optical materials. Herein, one kind of these materials may
be used singly, or a composite material consisting of these materials
may be used.
25
[0023]
The polycarbonate can be obtained by a method of causing a
reaction between an alcohol and phosgene or a reaction between an
alcohol and chloroforrnate, or by a method of causing an ester exchange
13
reaction of a carbonic diester compound. It is also possible to use
general polycarbonate resins in the form of commercially available
products. As the commercially available products, a Panlite series
manufactured by Teijin Chemicals Ltd. and the like can be used. The
5 composition for an optical material of the present embodiment can
contain the polycarbonate as the resin for an optical material (b) .
[0024]
Examples of the poly (meth) acrylate include poly (meth) acrylates
of alkane polyols such as ethylene glycol di (meth) acrylate, propylene
10 glycol di(meth)acrylate, butylene glycol di(meth)acrylate,
neopentyl glycol di (meth) acrylate, hexylene glycol di (meth) acrylate,
trimethylolpropane tri(meth)acrylate, and pentaerythritol
tetra (meth) acrylate; polyoxyalkane polyol poly (meth) acrylates such
as diethylene glycol di(meth)acrylate, triethylene glycol
15 di(meth)acrylate, polyethylene glycol di(meth)acrylate,
dipropylene glycol di(meth)acrylate, polypropylene glycol
di(meth)acrylate, dibutylene glycol di(meth)acrylate, and
dipentaerythritol hexa(meth)acrylate; and the like.
The composition for an optical material of the present
20 embodiment can contain the poly(meth)acrylate as the resin for an
optical material (b) .
[ 0025]
The polyolefin is prepared by polymerizing at least one kind
of olefin selected from cx-olefins in the presence of a known catalyst
25 for olefin polymerization such as a Ziegler-Natta catalyst, a
metallocene catalyst, or a so-called post-metallocene catalyst. The
ex-olefin monomer may be composed of a single component, or may be
14
obtained by copolymerizing multiple components.
[0026]
In manufacturing the polyolefin, the polymerization reaction
of the olefin can be performed by a liquid-phase polymerization method
5 such as a solution polymerization, suspension polymerization, or bulk
polymerization, a gas-phase polymerization method, or other known
polymerization methods. For manufacturing the polyolefin,
liquid-phase polymerization methods such as solution polymerization
and suspension polymerization (slurry polymerization) are preferably
10 used, and a suspension polymerization (slurry polymerization) method
is more preferably used. For the polymerization, known conditions
can be applied as temperature or pressure conditions.
The composition for an optical material of the present
embodiment can contain the polyolefin as the resin for an optical
15 material (b).
[0027]
The cyclic polyolefin is prepared by polymerizing at least one
kind of cyclic olefin selected from cyclic olefins in the presence
of a knm-m catalyst for olefin polymerization. The cyclic polyolefin
20 may be composed of a single monomer, or may be obtained by
copolymerizing multiple components. As the cyclic polyolefin, Apel
(trademark) manufactured by Mitsui Chemicals, Inc. can be suitably
used because it has a high degree of transparency.
25
[0028]
The polyallyl is manufactured by polymerizing at least one kind
of allyl group-containing monomer selected from allyl
group-containing monomers in the presence of a known polymerization
5
15
catalyst generating a radical. As the allyl group-containing
monomers, allyl diglycol carbonates or diallyl phthalates are
commercially available in general, and these can be suitably used.
[0029]
The polyurethane urea is a product obtained by reacting a
polyurethane prepolymer and a diamine curing agent, and typical
examples thereof include TRIVEX (trademark) available from PPG
Industries, Inc. A polyurethane polyurea is a material having a high
degree of transparency and can be suitably used.
10 [0030]
The polyene-polythiol polymer is produced by addition
polymerization or ethylene chain-like polymerization of a polyene
compound having two or more ethylenic functional groups in a one
molecule and a polythiol compound having two or more thiol groups
15 in a one molecule.
[0031]
Examples of the polyene compound in the polyene-polythiol
polymer include allyl alcohol derivatives, esters of (meth)acrylic
acid and polyol, urethane acrylate, divinyl benzene, and the like.
20 At least one kind of these can be used. Examples of the allyl alcohol
derivatives include triallyl isocyanurate, triallyl cyanurate,
diallyl maleate, diallyl fumarate, diallyl adipate, diallyl
phthalate, triallyl trimellitate, tetraallyl pyromellitate,
glycerin diallyl ether, trimethy1ol propane diallyl ether,
25 pentaerythritol diallyl ether, sorbitol diallyl ether, and the like.
Examples of the polyol in the esters of a (meth)acrylic acid and a
polyol include ethylene glycol, propylene glycol, 1,4-butanediol,
-----------------------
16
1,6-hexanediol, glycerin, trimethylol propane, pentaerythritol,
sorbitol, and the like.
[0032]
The ring-opening metathesis polymer is a polymer obtained by
5 performing ring-opening polymerization of cyclic olefins by using
a catalyst. The cyclic olefins that can be subjected to the
ring-opening polymerization are not particularly limited as long as
they have a cyclic structure, and examples thereof generally include
monocyclic cycloalkenes, monocyclic cycloalkadienes, polycyclic
•
10 cycloalkenes, and polycyclic cycloalkadienes having 3 to 40 carbon
atoms. Specific examples of the monocyclic cycloalkenes include
cyclobutene, cyclopentene, cyclohexene, cyclooctene, and the like.
Examples of the monocyclic cycloalkadienes include cyclobutadiene,
1,3-cyclopentadiene, 1,3-cyclohexadiene, 1,4-cyclohexadiene,
15 1,5-cyclooctadiene, and the like. Examples of the polycyclic
cycloalkenes include norbornene,
tetracyclo [ 6. 2. 1. 1 3
'
6
• 02
'
7
] dodec-4-ene, and the like. Examples of
the polycyclic cycloalkadienes include norbornadiene,
dicyclopentadiene, and the like. These may be substituted with
20 oxygen, sulfur, halogen, or the like, and may be hydrogenated.
Preferable examples thereof include ARTON (trademark) of JSR
Corporation and the like.
[0033]
The polyester is obtained by condensation polymerization
25 performed in the presence of a knm-m catalyst for manufacturing
polyester, such as Lewis acid catalyst repr.esented by an antimony
or germanium compound, an organic acid, or an inorganic acid.
17
Specifically, the polyester refers to a polymer composed of At least
one kind selected from polyvalent carboxylic acids including a
dicarboxylic acid and ester-forming derivatives thereof and one, t>vo,
or more kinds .selected from polyols including glycol, a polymer
5 composed of a hydroxycarboxylic acid and an ester-forming derivative
the:ceof, or a polymer composed of a cyclic ester.
[0034]
Examples of the dicarboxylic acid include saturated aliphatic
dicarboxylic acids, such as oxalic acid, malonic acid, succinic acid,
10 glutaric acid, adipic acid, pimelic acid, suberic acid, azelaic acid,
sebacic acid, decanedicarboxylic acid, dodecanedicarboxylic acid,
tetradecanedicarboxylic acid, hexadecanedicarboxylic acid,
1,3-cyclobutanedicarboxylic acid, 1,3-cyclopentanedicarboxylic
acid, 1,2-cyclohexanedicarboxylic acid,
15 1, 3-cyclohexanedicarboxylic acid, 1, 4-cyclohexanedicarboxylic acid,
2, 5-norbornanedicarboxylic acid, and dimer acids, and ester-forming
derivatives thereof; unsaturated aliphatic dicarboxylic acids, such
as fumaric acid, maleic acid, and itaconic acid, and ester-forming
derivatives thereof; and aromatic dicarboxylic acids, such as
20 orthophthalic acid, isophthalic acid, terephthalic acid, 5- (alkaline
metal)sulfoisophthalic acid, diphenic acid, 1,3-naphthalene
dicarboxylic acid, 1,4-naphthalene dicarboxylic acid,
1,5-naphthalene dicarboxylic acid, 2,6-naphthalene dicarboxylic
acid, 2,7-naphthalene dicarboxylic acid, 4,4'-biphenyldicarboxylic
25 acid, 4,4'-biphenylsulfone dicarboxylic acid, 4,4'-biphenylether
dicarboxylic acid, 1,2-bis(phenoxy)ethane-p,p'-dicarboxylic acid,
pamoic acid, and anthracene dicarboxylic acid, and ester-forming
18
derivatives thereof. Among these dicarboxylic acids, terephthalic
acid and naphthalene dicarboxylic acid are preferable, and
2, 6-naphthalene dicarboxylic acid is particularly preferable, since
these makes the obtained polyester exhibit excellent properties and
5 the like. The polyester optionally contains other dicarboxylic acids
as constituents. Examples of the polyvalent carboxylic acids other
than these dicarboxylic acids include ethane tricarboxylic acid,
propane tricarboxylic acid, butane tetracarboxylic acid,
pyromellitic acid, trimellitic acid, trimesic acid,
10 3,4,3' ,4'-biphenyltetracarboxylic acid, ester-forming derivatives
thereof, and the like.
[0035]
Examples of the glycol include aliphatic glycols such as
ethylene glycol, 1,2-propylene glycol, 1,3-propylene glycol,
15 diethylene glycol, triethylene glycol, 1,2-butylene glycol,
1,3-butylene glycol, 2,3-butylene glycol, 1,4-butylene glycol,
1,5-pentanediol, neopentyl glycol, 1,6-hexanediol,
1,2-cyclohexanediol, 1,3-cyclohexanediol, 1,4-cyclohexanediol,
1,2-cyclohexanedimethanol, 1,3-cyclohexanedimethanol,
20 1,4-cyclohexanedimethanol, 1,4-cyclohexanediethanol,
1,10-decamethylene glycol, 1,12-dodecanediol, polyethylene glycol,
polytrimethylene glycol, and polytetramethylene glycol; and aromatic
glycols such as hydroquinone, 4,4'-dihydroxybisphenol,
1,4-bis(~-hydroxyethoxy)benzene,
25 1,4-bis(~-hydroxyethoxyphenyl)sulfone, bis(p-hydroxyphenyl)ether,
bis(p-hydroxyphenyl)sulfone, bis(p-hydroxyphenyl)methane,
1,2-bis(p-hydroxyphenyl)ethane, bisphenol A, bisphenol C,
19
2,5-naphtha1enediol, and glycols obtained by adding ethylene oxide
to the above glycols.
Among these glycols, ethylene glycol, 1,3-propylene glycol,
1, 4-butylene glycol, and 1, 4-cyclohexane dimethanol are preferable.
5 Examples of polyols other than these glycols include
trimethylolmethane, trirnethylolethane, trimethylolpropane,
pentaerythritol, glycerol, hexanetriol, and the like.
[0036)
As the polyester, polyethylene terephthalate, polybutylene
10 terephthalate, polypropylene terephthalate,
poly(1,4-cyclohexanedimethyleneterephthalte), polyethylene
naphthalate, polybutylene naphthalate, polypropylene naphthalate,
and copolymers thereof are preferable.
15
[0037)
The epoxy resin is a resin obtained by ring-opening
polymerization of an epoxy compound. Examples of the epoxy compound
include phenol-based epoxy compounds obtained by a condensation
reaction between an epihalohydrin compound and a polyvalent phenol
compound such as bisphenol A glycidyl ether or bisphenol F glycidyl
20 ether; alcohol-based epoxy compounds obtained by condensation
beh1een an epihalohydrin compound and a polyol compound such as
hydrogenated bisphenol A glycidyl ether, hydrogenated bisphenol F
glycidyl ether, or cyclohexanedimethano1; glycidyl ester-based epoxy
compounds obtained by condensation between an epihalohydrin compound
25 and a polyvalent organic compound such as
3,4-epoxycyclohexylmethyl-3' ,4'-epoxycyclohexane carboxylate or
1,2-hexahydrophthalic acid diglycidyl ester; amine-based epoxy
l
---------------
20
compounds obtained be condensation between a primary and secondary
amine compounds and an epihalohydrin compound; and the like. The
examples also include aliphatic polyvalent epoxy compounds such as
vinylcyclohexene diepoxide like 4-vinyl-1-cyclohexane diepoxide,
5 and the like.
[0038]
(Polymerizable compound (c))
In the present embodiment, the composition for an optical
material can contain the polymerizable compound (c) , and as the resin
10 obtained from the polymerizable compound (c), polyurethane,
polythiourethane, polysulfide, and the like can be preferably used.
These are materials (transparent resins) having a high degree of
transparency, and can be suitably used for optical materials.
15
[0039]
The polyurethane is obtained from a polyisocyanate compound and
a polyol compound as the polymerizable compound (c). The
polythiourethane is obtained from a polyisocyanate compound and a
polythiol compound as the polymerizable compound (c) . The
composition for an optical material can contain the follmling
20 polymerizable compound· (c) constituting those resins.
[0040]
Examples of the polyisocyanate compound include aliphatic
polyisocyanate compounds such as hexamethylene diisocyanate,
2,2,4-trimethylhexane diisocyanate, 2,4,4-trimethylhexamethylene
25 diisocyanate, lysine diisocyanatomethyl ester, lysine triisocyanate,
m-xylylene diisocyanate, a, a, a' ,a'-tetramethylxylylene
diisocyanate, bis(isocyanatomethyl)naphthalene, mesitylene
l
--------------------------
21
triisocyanate, bis(isocyanatomethy1)su1fide,
bis(isocyanatoethy1)su1fide, bis(isocyanatomethyl)disu1fide,
bis(isocyanatoethyl)disulfide, bis(isocyanatomethylthio)methane,
bis(isocyanatoethylthio)methane, bis(isocyanatoethylthio)ethane,
5 and bis(isocyanatomethylthio)ethane; alicyclic polyisocyanate
compounds such as isophorone diisocyanate,
bis(isocyanatomethyl)cyclohexane,
dicyclohexylmethane-4,4'-diisocyanate, cyclohexane diisocyanate,
methyl cyclohexane diisocyanate, .dicyclohexyldimethyl methane
10 isocyanate, 2,5-bis(isocyanatomethyl)bicyclo-[2.2.1]-heptane,
2,6-bis(isocyanatomethyl)bicyclo-[2.2.1]-heptane,
3,8-bis(isocyanatomethyl)tricyclodecane,
3,9-bis(isocyanatomethyl)tricyclodecane,
4,8-bis(isocyanatomethyl)tricyclodecane, and
15 4,9-bis(isocyanatomethyl)tricyclodecane; aromatic polyisocyanate
compounds such as diphenylsulfide-4,4'-diisocyanate; heterocyclic
polyisocyanate compounds such as 2,5-diisocyanatothiophene,
2,5-bis(isocyanatomethyl)thiophene,
2,5-diisocyanatotetrahydrothiophene,
20 2,5-bis(isocyanatomethyl)tetrahydrothiophene,
3,4-bis(isocyanatomethyl)tetrahydrothiophene,
2,5-diisocyanato-1,4-dithiane,
2,5-bis(isocyanatomethyl)-1,4-dithiane,
4,5-diisocyanato-1,3-dithiolane, and
25 4,5-bis(isocyanatomethyl)-1,3-dithiolane; and the like.
[0041]
The polyol compound includes one or more kinds of aliphatic or
-----------------------
22
alicyclic alcohols. Specific examples thereof include linear or
branched aliphatic alcohols, alicyclic alcohols, alcohols obtained
by adding ethylene oxide, propylene oxide, or £-caprolactone to those
alcohols, and the like.
5 [0042]
Examples of the linear or branched aliphatic alcohols include
ethylene glycol, diethylene glycol, triethylene glycol, propylene
glycol, dipropylene glycol, tripropylene glycol, 1,3-propanediol,
2,2-dimethyl-1,3-propanediol, 2,2-diethyl-1,3-propanediol,
10 1,2-butanediol, 1,3-butanediol, 1,4-butanediol,
3-methyl-1,3-butanediol, 1,2-pentanediol, 1,3-pentanediol,
1,5-pentanediol, 2,4-pentanediol, 2-methyl-2,4-pentanediol,
3-methyl-1,5-pentanediol, 1,6-hexanediol, 2,5-hexanediol, glycerol,
diglycerol, polyglycerol, trimethylolpropane, pentaerythritol,
15 di(trimethylolpropane), and the like.
[ 0043]
Examples of the alicyclic alcohols include 1, 2-cyclopentanediol,
1,3-cyclopentanediol, 3-methyl-1,2-cyclopentanediol,
1,2-cyclohexanediol, 1,3-cyclohexanediol, 1,4-cyclohexanediol,
20 4,4'-bicyclohexanol, 1,4-cyclohexanedimethanol, and the like.
[0044]
Furthermore, compounds obtained by adding ethylene oxide,
propylene oxide, or £-caprolactone to the aforementioned alcohols
may be used. Examples thereof include ethylene oxide adducts of
25 glycerol, ethylene oxide adducts of trimethylolpropane, ethylene
oxide adducts of pentaerythritol, propylene oxide adducts of glycerol,
propylene oxide adducts of trimethylolpropane, propylene oxide
5
23
adducts of pentaerythritol, caprolactone-modified glycerol,
caprolactone-modified trimethylolpropane, caprolactone-modified
pentaerythritol, and the like.
[0045]
Examples of the polythiol compound include aliphatic polythiol
compounds such as methane dithiol, 1,2-ethanedithiol,
1,2,3-propanetrithiol, 1,2-cyclohexanedithiol,
bis(2-mercaptoethyl)ether, tetrakis(mercaptomethyl)methane,
diethylene glycol bis(2-mercaptoacetate), diethylene glycol
10 bis (3-mercaptopropionate), ethylene glycol bis (2-mercaptoacetate),
ethylene glycol bis(3-mercaptopropionate), trimethylolpropane
tris(2-mercaptoacetate), trimethylolpropane
tris(3-mercaptopropionate), trimethylolethane
tris(2-mercaptoacetate), trimethylolethane
15 tris(3-mercaptopropionate), pentaerythritol
tetrakis(2-mercaptoacetate), pentaerythritol
tetrakis(3-mercaptopropionate), bis(mercaptomethyl)sulfide,
bis(mercaptomethyl)disulfide, bis(mercaptoethyl)sulfide,
bis(mercaptoethyl)disulfide, bis(mercaptopropyl)sulfide,
2 0 bi s (mercaptomethy l thio) methane, bi s ( 2 -rnercaptoethy l thio) methane,
bis(3-mercaptopropylthio)methane,
1,2-bis(mercaptomethylthio)ethane,
1,2-bis(2-mercaptoethylthio)ethane,
1,2-bis(3-mercaptopropylthio)ethane,
25 1,2,3-tris(mercaptornethylthio)propane,
1,2,3-tris(2-rnercaptoethylthio)propane,
1,2,3-tris(3-mercaptopropylthio)propane,
l
24
4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane,
5,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane,
4,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane,
4,8-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane,
5 tetrakis(mercaptomethylthiomethyl)methane,
tetrakis(2-mercaptoethylthiomethyl)methane,
tetrakis(3-mercaptopropylthiomethyl)methane,
bis(2,3-dimercaptopropyl)sulfide,
2,5-dimercaptomethyl-1,4-dithiane, 2,5-dimercapto-1,4-dithiane,
10 2,5-dimercaptomethyl-2,5-dimethyl-1,4-dithiane, esters of
thioglycolic acids thereof and mercaptopropionic acids,
hydroxymethyl sulfide bis(2-mercaptoacetate), hydroxymethyl
sulfide bis(3-mercaptopropionate), hydroxyethyl sulfide
bis(2-mercaptoacetate), hydroxyethyl sulfide
15 bis(3-mercaptopropionate), hydroxymethyl disulfide
bis(2-mercaptoacetate), hydroxymethyl disulfide
bis(3-mercaptopropionate), hydroxyethyl disulfide
bis(2-mercaptoacetate), hydroxyethyl disulfide
bis(3-mercaptopropionate), 2-mercaptoethyl ether
20 bis(2-mercaptoacetate), 2-mercaptoethyl ether
bis(3-mercaptopropionate), thiodiglycolic acid
bis(2-mercaptoethylester), thiodipropionic acid
bis(2-mercaptoethylester), dithiodiglycolic acid
bis(2-mercaptoethylester), dithiodipropionic acid
25 bis (2-mercaptoethylester),
1,1,3,3-tetrakis(mercaptomethylthio)propane,
1,1,2,2-tetrakis(mercaptomethylthio)ethane,
25
4,6-bis(mercaptomethylthio)-1,3-dithiane,
tris(mercaptomethylthio)methane, and
tris(mercaptoethylthio)methane; aromatic polythiol compounds such
as 1,2-dimercaptobenzene, 1,3-dimercaptobenzene,
5 1,4-dimercaptobenzene, 1,2-bis(mercaptomethyl)benzene,
1,3-bis(mercaptomethyl)benzene, 1,4-bis(mercaptomethyl)benzene,
1,2-bis(mercaptoethyl)benzene, 1,3-bis(mercaptoethyl)benzene,
1,4-bis(mercaptoethyl)benzene, 1,3,5-trimercaptobenzene,
1,3,5-tris(mercaptomethyl)benzene,
10 1,3,5-tris(mercaptomethyleneoxy)benzene,
1,3,5-tris(mercaptoethyleneoxy)benzene, 2,5-toluenedithiol,
3,4-toluenedithiol, 1,5-naphtha1eneditihol, and
2,6-naphthaleneditihol; heterocyclic polythiol compounds such as
2-methylamino-4,6-dithiol-sym-triazine, 3,4-thiophenedithiol,
15 bismuthiol, 4,6-bis(mercpatomethylthio)-1,3-dithiane, and
2- (2, 2-bis (mercaptomethy1thio) ethyl) -1, 3-dithietane; and the like.
[0046]
In the present embodiment, when the polyurethane or
polythiourethane are prepared, a polymerization catalyst may or may
20 not be used. Furthermore, optional additives such as an internal
release agent and a bluing agent may be used.
[0047]
The polysulfide can be obtained by a method of performing
ring-opening polymerization of a polyepithio compound or a
25 polythietane compound as the polymerizable compound (c), or can be
obtained from a polyepithio compound and a polythiol compound. The
composition for an optical material can contain the following
l
26
polymerizable compound (c) constituting those resins.
[0048]
Examples of the polyepithio compound include epithioethylthio
compounds such as bis(1,2-epithioethyl)sulfide,
5 bis(l,2-epithioethyl)disulfide, bis(epithioethylthio)methane,
bis(epithioethylthio)benzene,
bis[4-(epithioethylthio)phenyl]sulfide, and
bis[4-(epithioethylthio)phenyl]methane; chain-like aliphatic
2,3-epithiopropylthio compounds such as
10 bis(2,3-epithiopropyl)sulfide, bis(2,3-epithiopropyl)disulfide,
bis(2,3-epithiopropylthio)methane,
1,2-bis(2,3-epithiopropylthio)ethane,
1,2-bis(2,3-epithiopropylthio)propane,
1,3-bis(2,3-epithiopropylthio)propane,
15 1,3-bis(2,3-epithiopropylthio)-2-methylpropane,
1,4-bis(2,3-epithiopropylthio)butane,
1,4-bis(2,3-epithiopropylthio)-2-methylbutane,
1,3-bis(2,3-epithiopropylthio)butane,
1,5-bis(2,3-epithiopropylthio)pentane,
20 1,5-bis(2,3-epithiopropylthio)-2-methylpentane,
1,5-bis(2,3-epithiopropylthio)-3-thiapentane,
1,6-bis(2,3-epithiopropylthio)hexane,
1,6-bis(2,3-epithiopropylthio)-2-methylhexane,
1,8-bis(2,3-epithiopropylthio)-3,6-dithiaoctane,
25 1,2,3-tris(2,3-epithiopropylthio)propane,
2,2-bis(2,3-epithiopropylthio)-1,3-bis(2,3-epithiopropylthiometh
yl)propane,
--------------------------------------
27
2,2-bis(2,3-epithiopropylthiomethyl)-1-(2,3-epithiopropylthio)bu
tane,
1,5-bis(2,3-epithiopropylthio)-2-(2,3-epithiopropylthiomethyl)-3
-thiapentane,
5 1,5-bis(2,3-epithiopropylthio)-2,4-bis(2,3-epithiopropylthiometh
yl)-3-thiapentane,
1-(2,3-epithiopropylthio)-2,2-bis(2,3-epithiopropylthiomethyl)-4
-thiahexane,
1,5,6-tris(2,3-epithiopropylthio)-4-(2,3-epithiopropylthiomethyl
10 )-3-thiahexane,
1,8-bis(2,3-epithiopropylthio)-4-(2,3-epithiopropylthiomethyl)-3
,6-dithiaoctane,
1,8-bis(2,3-epithiopropylthio)-4,5-bis(2,3-epithiopropylthiometh
yl)-3,6-dithiaoctane,
15 1,8-bis(2,3-epithiopropylthio)-4,4-bis(2,3-epithiopropylthiometh
yl)-3,6-dithiaoctane,
1,8-bis(2,3-epithiopropylthio)-2,5-bis(2,3-epithiopropylthiometh
yl)-3,6-dithiaoctane,
1,8-bis(2,3-epithiopropylthio)-2,4,5-tris(2,3-epithiopropylthiom
20 ethyl)-3,6-dithiaoctane,
1,1,1-tris[[2-(2,3-epithiopropylthio)ethyl]thiomethyl]-2-(2,3-ep
ithiopropylthio)ethane,
1,1,2,2-tetrakis[[2-(2,3-epithiopropylthio)ethyl]thiomethyl]etha
ne,
25 1,11-bis(2,3-epithiopropylthio)-4,8-bis(2,3-epithiopropylthiomet
hyl)-3,6,9-trithiaundecane,
1,11-bis(2,3-epithiopropylthio)-4,7-bis(2,3-epithiopropylthiomet
28
hyl)-3,6,9-trithiaundecane, and
1,11-bis(2,3-epithiopropylthio)-5,7-bis(2,3-epithiopropylthiomet
hyl)-3,6,9-trithiaundecane; cyclicaliphatic2,3-epithiopropylthio
compounds such as l,3-bis(2,3-epithiopropylthio)cyclohexane,
5 l,4-bis(2,3-epithiopropylthio)cyclohexane,
l,3-bis(2,3-epithiopropylthiomethyl)cyclohexane,
1,4-bis(2,3-epithiopropylthiomethyl)cyclohexane,
2,5-bis(2,3-epithiopropylthiomethyl)-1,4-dithiane,
2,5-bis[[2-(2,3-epithiopropylthio)ethyl]thiomethyl]-1,4-dithiane,
10 and
2,5-bis(2,3-epithiopropylthiomethyl)-2,5-dimethyl-1,4-dithiane;
aromatic 2,3-epithiopropylthio compounds such as
1,2-bis(2,3-epithiopropylthio)benzene,
1,3-bis(2,3-epithiopropylthio)benzene,
15 1,4-bis(2,3-epithiopropylthio)benzene,
1,2-bis(2,3-epithiopropylthiomethyl)benzene,
1,3-bis(2,3-epithiopropylthiomethyl)benzene,
1,4-bis(2,3-epithiopropylthiomethyl)benzene,
bis-[4-(2,3-epithiopropylthio)phenyl]methane,
20 2,2-bis[4-(2,3-epithiopropylthio)phenyl]propane,
bis[4-(2,3-epithiopropylthio)phenyl]sulfide,
bis[4-(2,3-epithiopropylthio)phenyl]sulfone, and
4,4'-bis(2,3-epithiopropylthio)biphenyl; chain-like aliphatic
2, 3-epithiopropyloxy compounds such as bis (2, 3-epi thiopropyl) ether,
25 bis (2, 3-epithiopropyloxy)methane,
1,2-bis(2,3-epithiopropyloxy)ethane,
1,2-bis(2,3-epithiopropyloxy)propane,
29
1,3-bis(2,3-epithiopropyloxy)propane,
1,3-bis(2,3-epithiopropyloxy)-2-methyl propane,
1,4-bis(2,3-epithiopropyloxy)butane,
1,4-bis(2,3-epithiopropyloxy)-2-methyl butane,
5 1,3-bis(2,3-epithiopropyloxy)butane,
1,5-bis(2,3-epithiopropyloxy)pentane,
1,5-bis(2,3-epithiopropyloxy)-2-methyl pentane,
1,5-bis(2,3-epithiopropyloxy)-3-thiapentane,
1,6-bis(2,3-epithiopropyloxy)hexane,
10 1,6-bis(2,3-epithiopropy1oxy)-2-methyl hexane,
1~8-bis(2,3-epithiopropyloxy)-3,6-dithiaoctane,
1,2,3-tris(2,3-epithiopropyloxy)propane,
2,2-bis(2,3-epithiopropyloxy)-1,3-bis(2,3-epithiopropyloxymethyl
)propane,
15 2,2-bis(2,3-epithiopropyloxymethyl)-1-(2,3-epithiopropyloxy)buta
ne,
1,5-bis(2,3-epithiopropyloxy)-2-(2,3-epithiopropyloxymethyl)-3-t
hiapentane,
1,5-bis(2,3-epithiopropyloxy)-2,4-bis(2,3-epithiopropyloxymethyl
20 )-3-thiapentane,
1-(2,3-epithiopropyloxy)-2,2-bis(2,3-epithiopropyloxymethyl)-4-t
hiahexane,
1,5,6-tris(2,3-epithiopropyloxy)-4-(2,3-epithiopropyloxymethyl)-
3-thiahexane,
25 1,8-bis(2,3-epithiopropyloxy)-4-(2,3-epithiopropyloxymethyl)-3,6
-dithiaoctane,
1,8-bis(2,3-epithiopropyloxy)-4,5-bis(2,3-epithiopropyloxymethyl
30
)-3,6-dithiaoctane,
1,8-bis(2,3-epithiopropyloxy)-4,4-bis(2,3-epithiopropyloxymethyl
)-3,6-dithiaoctane,
1,8-bis(2,3-epithiopropyloxy)-2,5-bis(2,3-epithiopropyloxymethyl
5 )-3,6-dithiaoctane,
1,8-bis(2,3-epithiopropyloxy)-2,4,5-tris(2,3-epithiopropyloxymet
hyl)-3,6-dithiaoctane,
1,1,1-tris[[2-(2,3-epithiopropyloxy)ethyl]thiomethy1]-2-(2,3-epi
thiopropy1oxy)ethane,
10 1,1,2,2-tetrakis[[2-(2,3-epithiopropyloxy)ethy1]thiomethy1]ethan
e,
1,11-bis(2,3-epithiopropyloxy)-4,8-bis(2,3-epithiopropyloxymethy
1)-3,6,9-trithiaundecane,
1,11-bis(2,3-epithiopropyloxy)-4,7-bis(2,3-epithiopropyloxymethy
15 1)-3,6,9-trithiaundecane, and
1,11-bis(2,3-epithiopropyloxy)-5,7-bis(2,3-epithiopropy1oxymethy
1)-3,6,9-trithiaundecane; cyclic aliphatic 2,3-epithiopropyloxy
compounds such as 1,3-bis(2,3-epithiopropyloxy)cyclohexane,
1,4-bis(2,3-epithiopropyloxy)cyclohexane,
20 1,3~bis(2,3-epithiopropy1oxymethyl)cyclohexane,
1,4-bis(2,3-epithiopropyloxymethyl)cyclohexane,
2,5-bis(2,3-epithiopropyloxymethy1)-1,4-dithiane,
2,5-bis[[2-(2,3-epithiopropyloxy)ethyl]thiomethyl]-1,4-dithiane,
and
25 2,5-bis(2,3-epithiopropyloxymethyl)-2,5-dimethyl-1,4-dithiane;
aromatic 2,3-epithiopropyloxy compounds such as
1,2-bis(2,3-epithiopropyloxy)benzene,
31
1,3-bis(2,3-epithiopropyloxy)benzene,
1,4-bis(2,3-epithiopropyloxy)benzene,
1,2-bis(2,3-epithiopropyloxymethyl)benzene,
1,3-bis(2,3-epithiopropyloxymethyl)benzene,
5 1,4-bis(2,3-epithiopropyloxymethyl)benzene,
bis[4-(2,3-epithiopropyloxy)phenyl]methane,
2,2-bis[4-(2,3-epithiopropyloxy)phenyl]propane,
bis[4-(2,3-epithiopropyloxy)phenyl]sulfide,
bis(4-(2,3-epithiopropyloxy)phenyl]sulfone, and
10 4,4'-bis(2,3-epithiopropyloxy)biphenyl; and the like.
[0049]
As the polythietane compound, metal-containing thietane
compounds or non-metallic thietane compounds can be used.
As disclosed in W02005-95490 or Japanese Unexamined Patent
15 Publication No. 2003-327583, these polythietane compounds contain
one or more thietanyl groups in a molecule. Among the polythietane
compounds, compounds having two or more thietanyl groups in total
are preferable, and examples thereof include sulfide-based thietane
compounds such as bisthietanyl sulfide,
20 bis(3-thietanylthio)disulfide, bis(3-thietanylthio)methane, and
3-( ((3'-thietanylthio)methylthio)methylthio)thietane;
polysulfide~based thietane compounds such as
bis(3-thietanyl)disulfide, bis(3-thietanyl)trisulfide,
bis(3-thietanyl)tetrasulfide, and bis(3-thietanyl)pentasulfide;
25 and the like.
[0050]
The polymerizable compound (c) is preferably a combination of
32
a polyisocyanate compound and a polyol compound, a combination of
a polyisocyanate compound and a polythiol compound, a polyepithio
compound and/or a polythietane compound, or a combination of a
polyepithio compound and a polythiol compound.
5 [0051]
Next, the composition for an optical material of the present
embodiment will be specifically described.
The composition for an optical material of the present
10 embodiment contains one or more kinds of ultraviolet absorber (a)
having a maximum absorption peak within a range of equal to or greater
than 350 nm and equal to or less than 370 nm, and a resin for an optical
material (b) or a polymerizable compound (resin monomer) (c).
The amount of the ultraviolet absorber (a) contained in the
15 composition can be 0. 3% by weight to 2% by weight, preferably 0. 3%
by weight to 1.5% by weight, and more preferably 0.3% by weight to
1.2% by weight, with respect to the total weight of the resin for
an optical material (b) or the polymerizable compound (c).
20
[0052]
When the composition for an optical material containing the
ultraviolet absorber (a), Hhich have a maximum absorption peak within
a predetermined rang, in an amount within the aforementioned range
is used, it is possible to obtain an optical material satisfying the
aforementioned characteristics (1) to (3) of light transmittance at
25 a specific 1-1avelength.
The optical material obtained from the composition for an
optical material of the present embodiment has excellent transparency,
33
is inhibited from being colored, and can prevent injury including
eyefatigueorstress. Particularly, because the light transmittance
thereof at 440 nm is equal to or greater than 80%, the optical material
can be obtained in the form of a colorless and transparent optical
5 material having excellent external appearance.
[0053]
The composition for an optical material of the present
embodiment may further contain an internal release agent, a
resin-modifying agent, a light stabilizer, a bluing agent, and the
10 like as other components. Moreover, the composition for an optical
material can contain knm-m ultraviolet absorbers having a maximum
absorption peak that is not within a range of equal to or greater
than 350 nm and equal to or less than 370 nm, in addition to the
ultraviolet absorber (a) .
15 [0054]
(Other components)
(Internal release agent)
As the internal release agent, acidic phosphoric acid esters
can be used. Examples of the acidic phosphoric acid esters include
20 a phosphoric acid monoester and a phosphoric acid diester. One kind
thereof can be used singly, or two or more kinds thereof can be used
by being mixed with each other.
E'or example, it is possible to use ZelecUN manufactured by Stepan
Company, internal release agents for MR manufactured by Mitsui
25 Chemicals, Inc., a JP series manufactured by JOHOKU CHEMICAL CO.,
LTD., a Phosphanol series manufactured by TOHO Chemical Industry Co.,
Ltd., an AP or DP series manufactured by DAIHACHI CHEMICAL INDUSTRY
CO., LTD., and the like.
[0055]
(Resin-modifying agent)
34
Furthermore, in order to adjust various properties of the
5 obtained resin, such as optical properties, impact resistance, and
specific gravity, and to adjust viscosity or pot life of the
composition, a resin-modifying agent can be added to the
polymerizable composition of the present invention, l·lithin a range
that does not diminish the effects of the present invention.
10
15
Examples of the resin-modifying agent include olefin compounds
and the like including episulfide compounds, alcohol compounds, amine
compounds, epoxy compounds, organic acids and anhydrides thereof,
and (meth)acrylate compounds.
[0056]
(Light stabilizer)
As the light stabilizer, hindered amine-based compounds can be
used. Examples of commercially available products of the hindered
amine compounds include LoNilite76 and Lowilite92 manufactured by
Chemtura Corporation, Tinuvin144, Tinuvin292, and Tinuvin765
20 manufactured by BASF Corporation, Adeka Stab LA-52 and LA-72
25
manufactured by ADEKA CORPORATION, JF-95 manufactured by JOHOKU
CHEMICAL CO., LTD., and the like.
[0057]
(Bluing agent)
Examples of the bluing agent include substances that have an
absorption band in a Navelength range from orange to yelloN Nithin
a visible light region and functions to adjust the color of an optical
35
material formed of a resin. More specifically, the bluing agent
contains substances that are blue and violet in color.
[0058]
The composition for an optical material can be obtained by mixing
5 the aforementioned components together by a predetermined method.
The respective components in the composition can be mixed in
known order by a known method without particular limitation, as long
as the components can be uniformly mixed together. Examples of the
known method include a method of preparing a master batch containing
10 additives in a predetermined amount and dispersing and dissolving
the master batch in a solvent, and the like. For example, in the
case of the polyurethane resin, a method of preparing a master batch
by dispersing and dissolving additives in the polyisocyanate compound,
and the like can be used.
15 In the present embodiment, in order to obtain a polyurethane
and polythiourethane, a polymerization catalyst may or may not be
used.
[0059]
Specifically, the optical material of the present embodiment
20 can be obtained by a method of curing the composition for an optical
material containing the ultraviolet absorber (a) and the resin for
an optical material (b) or by a method of mixing the composition for
an optical material containing the ultraviolet absorber (a) and the
polymerizable compound (c) and then polymerizing the composition.
25 [0060]