SPECIFICATION
OPTICAL MATERIAL AND USE THEREOF
5 TECHNICAL FIELD
The present invention r e l a t e s t o an o p t i c a l mat&ial and use
thereof. More s p e c i f i c a l l y , the present invention r e l a t e s t o a
composition for an o p t i c a l m a t e r i a l andanopticalproduct containing
10 a molded product which is formed by molding the composition for an
o p t i c a l material.
BACKGROUND ART
[0002]
15 Eyes are dazzled by l i g h t from a streetlamp or from a headlight
of a vehicle a t night, and therefore, v i s i b i l i t y of an object is
d e t e r i o r a t e d . Furthermore, l i g h t is i r r e g u l a r l y reflected by a w e t
road surface or raindrops during r a i n f a l l , and therefore, v i s i b i l i t y
of an object is f u r t h e r deteriorated. It is considered t h a t t h i s
20 is because light having a wavelength of 482 nm as a center a c t s on
a photoreceptor within the eyes, pupillary l i g h t reflex is prompted,
and the pupil is contracted t o suppress incidence of l i g h t i n t o the
eyes.
25 Patent Document l d i s c l o s e s a visiondevice using a p o l a r i z a t i o n
f i l t e r and a colored sheet in combination. In Patent Document 1,
it is also disclosed t h a t it is possible to improve v i s i b i l i t y a t
night during r a m f a l l .
[00041
PatentDocument2 discloses a spectacle frame with illumination
inwhich illumination is i n s t a l l e d i n t h e spectacle frame. In Patent
5 Document 2, it is also disclosed t h a t it is possible t o improve
v i s i b i l i t y of an object a t night or i n a dark place by illuminating
the front of the eyes with illumination.
Patent Document 3 discloses a n o p t i c a l f i l t e r w h i c h selectively
absorbs l i g h t of a s p e c i f i c wavelength, and l i g h t shielding
10 spectacles using the o p t i c a l f i l t e r .
[00051
Patent Document 4 discloses a display f i l t e r containing a
specificporphyrincompound. PatentDocument5disclosesa spectacle
lens containing a s p e c i f i c porphyrin compound.
15 RELATED DOCUMENT
PATENT DOCUMENT
[0006]
[Patent Document11 JapaneseUnexamined Patent PublicationNo.
6-72151
20 [PatentDocument2] Japanese Unexamined Patent Publication No.
2004-163839
[PatentDocument31 JapaneseUnexamined Patent PublicationNo.
2012-63715
[PatentDocument4] JapaneseUnexaminedPatent PublicationNo.
25 2008-239592
[PatentDocument5] Japanese Unexamined Patent PublicationNo.
2011-237730
SUMMARY OF THE INVENTION
[0007]
However, the vision device disclosed in Patent Document 1 uses
5 a pigment and a polarization sheet, which absorbs incident light,
in combination, and therefore, there is a problem in that an object
appears to be dark. This is still an unavoidable problem in terms
of a mechanism of action even if a yellow pigment is used.
[0008]
10 The spectacle frame disclosed in Patent Document 2 has an
illumination device comprised of a battery and a lamp on the frame.
For this reason, spectacles, including the spectacle frame, become
heavy, and therefore, there is a problem with the sense of use, such
as a feeling of fatigue, when using the spectacles for a long period
15 of time.
[00091
In paragraph 0023 of Patent Document 3, an optical filter which
is produced using an optical multilayer film, an optical filter
comprised of a volume phase type hologram, and an optical filter
20 comprisedof~atransparentproduct in whichmetal microparticles are
mixed are disclosed. However, there are many problems in that metal
microparticles have to be used, a production process is complicated,
or the like.
However, there is no disclosure of improvement of visibility
25 of an object in darkness, in Patent Documents 4 and 5.
The present inventors have found an optical material in which
pupillary l i g h t reflex is suppressed and incidence of l i g h t i n t o the
eyes in darkness is a s s i s t e d by selectively absorbing l i g h t in a
wavelength range of 471 nm t o 490 nm, and therefore, an object in
darkness is more e a s i l y v i s i b l e .
5 The present invention can be represented as follows.
[00111
[ I ] An o p t i c a l material in which a transmittance curve measured a t
a thickness of 2 mmthereof s a t i s f i e s the following c h a r a c t e r i s t i c s
(1) t o ( 4 ) ,
10 (1) the transmittance curve has a maximum transmittance value
inawavelength rangeof400nmto 440nmandthemaximumtransmittance
thereof is 50% or more,
(2) the transmittance curve has a minimum transmittance value
i n a wavelength range of 471 nm t o 500 nm,
15 (3) the transmittance a t a wavelength of 540 nm is 60% or more,
and
(4) the minimum transmittance value i n the r~~avelengtrhan ge of
471 nm t o 500 nm is seven-tenths or less of the maximum transmittance
i n the wavelength range of 400 nm t o 440 nm and is seven-tenths or
20 less of the t ~ a n s m i t t a n c ea t 540 nm.
[21 The o p t i c a l material according to [ I ] ,
inwhichtheminimumtransmittancevalueinthewavelength range
of 471 nm t o 500 nm is 60% or less.
[31 The o p t i c a l material according to [ I ] or [21, including:
25 a t l e a s t one kind of organic dyes i n which an absorption peak
is in a wavelength range of 471 nm to 490 nm and the half-value width
of the absorption peak is 10 nm or more and l e s s than 50 nm, i n an
absorption spectrum which is measured a t an o p t i c a l path length of
10 rnm of a chloroform solution thereof a t a concentration of 0 . 0 1
g/L.
[4] The optical material according t o [3],
5 in which the amount of the organic dyes is 5 ppm to 100 ppm.
[5] The o p t i c a l material according t o [3] or [4],
in which the organic dyes are one or more compounds selected
from porphyrin-based compounds represented by the folloriing General
Formula ( A ) .
I n t h e formula, XltoX~eachindependentlyrepresentahydrogen
atom; astraightorbranchedalkylgroup; anethynylgroup; anethynyl
group substituted with t h e s t r a i g h t or branched alkyl group; an
ethynyl group having a phenyl group; or an ethynyl group having a
15 phenylgroup substituted with t h e s t r a i g h t or branched alkylgroup.
A l l of XI t o Xa are not hydrogen atoms a t same time. R1 t o Rq each
independently represent a hydrogen atom; and a s t r a i g h t or branched
alkylgroup. Mrepresentstwo hydrogenatoms, a divalentmetal atom,
a trivalent substituted metal atom, a tetravalent substituted metal
atom, a hydroxylated metal atom, or an oxidized metal atom.
[6] The optical material according to any one of [3] to [5],
5 including: at least one kind selected from polyurethane,
polythiourethane, polysulfide, polycarbonate, poly(meth)acrylate,
and polyolefin.
[7] The optical material according to any one of [3] to [6],
including: polythiourethane.
10 [8] The optical material according to [6] or 171,
inwhichthepolythiourethaneis comprisedofaconstituent unit
derivedfromapolyisocyanate compoundandaconstituentunitderived
from a polythiol compound,
in which the polyisocyanate compound is at least one kind
15 selected from 2,5-bis(isocyanatomethyl)bicyclo-[2.2.1]-heptane,
2,6-bis(isocyanatomethyl)bicyclo-[2.2.1]-heptane, m-xylylene
diisocyanate, dicyclohexylmethane diisocyanate,
1,3-bis(isocyanatomethyl)cyclohexane,
1,4-bis(isocyanatomethyl)cyclohexane, isophorone diisocyanate,
20 1,6-hexamethylene diisocyanate, and 1,5-pentamethylene
diisocyanate, and
in which the polythiol compound is at least one kind selected
from 4-mercaptomethyl-l,8-dimercapto-3,6-dithiaoctane,
5,7-dimercaptomethyl-l,ll-dimercapto-3,6,9-trithiaundecane,
25 4,7-dimercaptomethyl-l,1l-dimercapto-3,6,9-trithiaundecane,
4,8-dimercaptomethyl-l,ll-dimercapto-3,6,9-trithiaundecane,
pentaerythritol tetrakis(3-mercaptopropionate),
bis (mercaptoethyl)s ulfide, pentaerythritol -
tetrakis(2-mercaptoacetate), 2,5-bis(mercaptomethy1)-1,4-dithiane,
1,1,3,3-tetrakis (mercaptomethylthio)propane,
4,6-bis (mercaptomethylthio)- 1,3-dithiane, and
5 2- (2,2-bis( mercaptomethylthio)e thyl)- 1,3-dithietane.
[9] A composition for an optical material, including:
a resin for an optical material or a resin monomer; and
at least one kind of organic dyes in which an absorption peak
is in a wavelength range of 471 nm to 490 nm and the half-value width
10 of the absorption peak is 10 nm or more and less than 50 nm, in an
absorption spectrum which is measured at an optical path length of
10 mm of a chloroform solution thereof at a concentration of 0.01
g/L,
in which the amount of the organic pigment is 0.0005 parts by
15 weight to 0.01 parts by weight with respect to 100 parts by weight
in total of the resin for an optical material or the resin monomer.
[lo] The composition for an optical material according to [9],
in which the organic dyes are one or more compounds selected
fromporphyrin-based compounds represented by the following General
20 Formula (A).
I n t h e formula, X1toXgeachindependentlyrepresentahydrogen
atom; astraightorbranchedalkylgroup; anethynylgroup; anethynyl
group substituted with t h e s t r a i g h t or branched alkyl group; an
5 ethynyl group having a phenyl group; or an ethynyl group having a
phenyl group substituted with the s t r a i g h t or branched alkyl group.
A l l of XI t o Xg are not hydrogen atoms a t same time. R1 to Rq each
independently represent a hydrogen atom; and a s t r a i g h t or branched
alkylgroup. Mrepresentstwohydrogen atoms, adivalentmetalatom,
10 a t r i v a l e n t s u b s t i t u t e d metal atom, a t e t r a v a l e n t substituted metal
atom, a hydroxylated metal atom, or an oxidized metal atom.
[Ill The composition for an o p t i c a l material according to [9] or
[ l o ] ,
in which the resin for an optical material is a t l e a s t one kind
15 selected from polyurethane, polythiourethane, polysulfide,
polycarbonate, poly(meth)acrylate, and polyolefin.
[12] The composition for an optical material according t o any one
of [9] to [Ill, ~ ~~~
in which the resin for an optical material is polythiourethane.
[13] The composition for an optical material according to any one
5 in which the resin monomer is a polyisocyanate compound and a
polythiol compound.
1141 The composition for an optical material according to [13],
in which the polyisocyanate compound is at least one kind
selected from 2,5-bis(isocyanatomethyl)hicyclo-[2.2.1]-heptane,
10 2,6-bis(isocyanatomethyl)bicyclo-[2.2.1]-heptane, m-xylylene
diisocyanate, dicyclohexylmethane diisocyanate,
1,3-his (isocyanatomethyl)c yclohexane,
1,4-bis(isocyanatomethyl)cyclohexane, isophorone diisocyanate,
1,6-hexamethylene diisocyanate, and 1,5-pentamethylene
15 diisocyanate, and
in which the polythiol compound is at least one kind selected
from 4-mercaptomethyl-l,8-dimercapto-3,6-dithiaoctane,
20 4,8-dimercaptomethyl-l,ll-dimercapto-3,6,9-trithiaundecane,
pentaerythritol tetrakis(3-mercaptopropionate),
bis(mercaptoethyl)sulfide, pentaerythritol
tetrakis(2-mercaptoacetate), 2,5-bis(mercaptomethy1)-1,4-dithiane,
1,1,3,3-tetrakis (mercaptomethylthio)propane,
25 4,6-bis (mercaptomethylthio) -1,3-dithiane, and
2- (2,2-bis (mercaptomethylthio) ethyl) -1,3-dithietane.
[I51 A process for producing a molded product, including:
a step of obtaining the cornposition for an optical material
according to any one of [91 to [I41 by mixing the organic dyes with
the resin for an optical material or the resin monomer; and
a step of curing the composition for an optical material.
5 [I61 The process for producing a molded product according to [15],
in which the resin monomer is a polyisocyanate compound and a
polythiol compound.
[I71 The process for producing a molded product according to [I51
or [161,
10 in which the resin monomer is the polyisocyanate compound and
the polythiol compound,
in which the polyisocyanate compound is at least one kind
selected from 2,5-bis (isocyanatomethyl)b icyclo- r2.2.11 -heptane,
2,6-bis(isocyanatomethyl)bicyclo-[2.2.1]-heptane, m-xylylene
15 diisocyanate, dicyclohexylmethane diisocyanate,
1,3-bis(isocyanatomethyl)cyclohexane,
1,4-bis(isocyanatomethyl)cyclohexane, isophorone diisocyanate,
1,6-hexamethylene diisocyanate, and 1,5-pentamethylene
diisocyanate, and
2 0 in which the polythiol compound is at least one kind selected
from 4-mercaptomethyl-l,8-dimercapto-3,6-dithiaoctane,
5,7-dimercaptomethyl-l,1l-dimercapto-3,6,9-trithiaundecane,
4,7-dimercaptomethyl-l,ll-dimercapto-3,6,9-trithiaundecane,
4,8-dimercaptomethyl-l,ll-dimercapto-3,6,9-trithiaundecane,
25 pentaerythritol tetrakis(3-mercaptopropionate),
bis(mercaptoethyl)sulfide, pentaerythritol
tetrakis(2-mercaptoacetate), 2,5-bis(mercaptomethy1)-1,4-dithiane,
. - 1,1,3,3-tetrakis (mercaptomethylthio)propane,
4,6-his (mercaptomethylthio)- 1,3-dithiane, and
2-(2,2-bis(mercaptomethylthio)ethyl)-1,3-dithietane.
[I81 A molded product which is obtained by polymerizing and curing
5 the composition for an optical material according to any one of [9]
to [14].
1191 An optical material comprised of the molded product according
to [19].
[20] A plastic spectacle lens comprised of the optical material
10 according to any one of [I] to [8] and 1191.
[21] A plastic spectacle lens,
inwhichalensbasematerialiscomprisedoftheopticalmaterial
according to any one of [I] to [ E l and [19].
1221 A film comprised of the molded product according to [18].
15 [23] A plastic spectacle lens, including:
a film layer over at least one surface of a lens base material,
in which the film layer is comprised of the film according to
t221.
I241 A plastic spectacle lens including:
in which the coating layer is comprised of the composition for
an optical. material according to any one of [91 to [14].
[00121
According to the optical material of the present invention, it
25 is possible to selectively absorb only light in a wavelength range
of 471nmto 490 nmandtoimprove visibilityofanobject in darkness
by suppressing pupillary light reflex and assisting incidence of
light into the eyes in darkness. Moreover, according to the optical
material ofthepresent invention, itispossibletoprovideaplastic
spectacle lens for an optical material which is excellent for
visibility of an object at night.
5 In addition, the optical material of the present invention
contains organic dyes which selectively absorb only light of a
specific wavelength, and therefore, can be easily produced
industrially.
10 BRIEF DESCRIPTION OF THE DRAWINGS
[0013]
The above-described purposes and other purposes, and
characteristics andadvantageswillbemade clearer through suitable
embodiments to be described below and the following accompanying
15 drawings.
[a0141
FIG. l shows transmittance curves of optical materials, with
a thickness of 2 mm, which have been measured in Examples 1 to 4.
FIG. 2 shows transmittance curves of optical materials, with
20 a thickness o5-2.mm, which have been measured in Examples 3 and 5
to 7.
FIG. 3 shows transmittance curves of optical materials, with
a thickness of 2 mm, which have been measured in Examples 3 and 8
to 12.
25 FIG. 4 shows transmittance curves of optical materials, with
a thickness of 2 mm, which have been measured in Example 3 and
Comparative examples 2 and 3.
DESCRIPTION OF EMBODIMENTS
[0015]
Hereinafter, an embodiment of the present invention will be
5 described in detail.
The optical material of the present embodiment satisfies the
following (1) to (4) in a transmittance curve which is measured at
a thickness of 2 mm of the optical material.
(1) the transmittance curve has a maximum transmittance value
10 inawavelengthrangeof400nmto 440nmandpreferablyinawavelength
range of 420 nm to 440 nm, and the maximum transmittance thereof is
50% or more.
(2) the transmittance curve has a minimum transmittance value
inawavelengthrangeof471nmto500nmandpreferablyinawavelength
15 range of 471 nm to 490 nm.
( 3 ) The transmittance at a r-ravelength of 540 nm is 60% or more
and preferably 65% or more.
(4) The minimum transmittance value in the wavelength range of
471 nm to 500 nm and preferably in the wavelength range of 471 nm
20 to 490 nm is,fseven-tenthso r less of the maximum transmittance in
the wavelength range of 400 nm to 440 nm and preferably in the
wavelength range of 420 nm to 440 nm, and is seven-tenths or less
of the transmittance at 540 nm.
Furthermore, it is preferable that the optical material of the
25 present embodiment satisfies the following characteristic ( 5 ) .
(5) The minimum transmittance value in the wavelength range of
471 nrn to 500 nm is 60% or less, preferably 50% or less, and more
preferably 45% or less, and p a r t i c u l a r l y preferably 40% or l e s s .
[0016]
The optical material of the present embodiment s a t i s f i e s the
above-described (1) to ( 4 ) and preferably ( 5 ) , and therefore, can
5 contain a t l e a s t one kind of organic pigment in which an absorption
peak is i n a wavelength range of 471 nm t o 490 nm and the half-value
width of the absorption peak is 10 nm or more and less than 50 nm,
i n an absorption spectrum which is measured a t an o p t i c a l path length
of 10 rnm of a chloroform solution thereof a t a concentration of 0.01
10 g/L.
F i r s t , the organic dyes w i l l be described below.
[OOlI]
[Organic Dyes]
Theorganicdyescontainedintheopticalmaterialofthepresent
15 embodiment are not p a r t i c u l a r l y limited as long as the organic dyes
s a t i s f y the above-described spectrumcharacteristicsmeasuredunder
the conditions, and it is preferable that the organic dyes have an
absorption peak in a range of 471 nm t o 490 nm and preferably i n a
range of 475 nm to 485 nun. Preferred examples of the organic dyes
20 include a porphyrin-based compound.
The porphyrin-based compound is represented by the following
General Formula (A).
[0018]
[00191
In the formula, XI to X8 each independently represent a hydrogen
atom; a straight or branched alkyl group; and a substituted or
5 unsubstituted ethynyl group. All of X1 to X8 are not hydrogen atoms
at same time. R1 to Rq each independently represent a hydrogen atom;
and a straight or branched alkyl group. M represents two hydrogen
atoms, a divalent metal atom, a trivalent substituted metal atom,
a tetravalent substituted metal atom, a hydroxylated metal atom, or
10 an oxidized ,metel, atom.
100201
Here, examples of the substituent group of the substituted
ethynyl group include an alkyl group, and a substituted or
unsubstituted phenyl group.
15 In General Formula (A), XI to Xg each independently represent
a hydrogenatom; a 1-12C straight orbranchedalkylgroup; an ethynyl
group substituted with the 1-12C straight or branched alkylgroup;
or an ethynyl group having a phenyl group s u b s t i t u t e d with the 1-12C
s t r a i g h t or branched alkyl g r o u p i o r an ethynyl group having an
unsubstituted phenyl group. A l l of XI t o Xg are not hydrogen atoms
a t same t i m e .
5 [0021]
Preferably, R1 t o Rq each independently represent a hydrogen
atom; and a 1-8C s t r a i g h t or branched alkyl group.
In addition, M is preferably Cu, Zn, Fe, Co, N i , Pt, Pd, Mn,
Mg, Mn(0H) , Mn(0H) Z, VO, or TiO.
10 [0022]
Morepreferably, X~toXgeachindependentlyrepresentahydrogen
atom; a 1-8C s t r a i g h t or branched alkyl group; an ethynyl group
s u b s t i t u t e d with the 1-8C s t r a i g h t or branched a l k y l group; or an
ethynyl group having a phenyl group substituted with a 1-6C s t r a i g h t
15 o r branched alkyl group.
In addition, M is more preferably Cu, Pt, Pd, N i , or VO and more
preferably N i or Pd.
Specific examples of XI t o Xg are described below.
2 0 In a ca.se:~.where X1 t o Xg a r e s t r a i g h t or branched alkyl groups,
examples of t h e s t r a i g h t or branched alkyl groups include a methyl
group, an e t h y l group, an n-propyl group, an isopropyl group, an
n-butyl group, an isobutyl group, a tert-butyl group, an n-pentyl
group, an isopentyl group, an neopentyl group, a t e r t - p e n t y l group,
25 a 1,2-dimethylpropyl group, a 1-methylbutyl group, a 2-methylbutyl
group, an n-hexyl group, a 2-methylpentyl group, a 4-methylpentyl
group, a 4-methyl-2-pentyl group, a 1,2-dimethylbutyl group, a
2,3-dimethylbutyl group, a 2-ethylbutyl group, an n-heptyl group,
a 3-methylhexyl group, a 5-methylhexyl group, a 2,4-dimethyl pentyl
group, an n-octyl group, a t e r t - o c t y l group, a 2-ethylhexyl group,
a 2-propylpentyl group, and a 2,5-dimethylhexyl group.
5 Among these, a methyl group, an ethyl group, an n-propyl group,
anisopropyl group, ann-butylgroup, anisobutylgroup, a t e r t - b u t y l
group, an n-pentyl group, an isopentyl group, an neopentyl group,
a 1,2-dimethylpropylgroup, a 1-methylbutyl group, ann-hexylgroup,
a l,2-dimethylbutyl group, a 2-ethylbutyl group, an n-heptyl group,
10 ann-octylgroup, anda2-ethylhexylgrouparepreferable, andamethyl
group, an ethyl group, an n-propyl group, an isopropyl group, an
n-butyl group, an isobutyl group, a t e r t - b u t y l group, an n-pentyl
group, an isopentyl group, an n-hexyl group, a 1,2-dimethylbutyl
group, a 2-ethylbutyl group, an n-heptyl group, and an n-octyl group
15 are more preferable.
to0241
In a case where XI t o Xe are substituted ethynyl groups, examples
of the s u b s t i t u t e d ethynyl groups include an ethynyl group having
a s t r a i g h t o r branched alkyl group such a s a methyl group, an ethyl
20 group, an n-propyl group, an isopropyl group, an n-butyl group, an
isobutyl group, a t e r t - b u t y l group, an n-pentyl group, an isopentyl
group, an neopentyl group, a t e r t - p e n t y l g r o u p , a 1,2-dimethylpropyl
group, a 1-methylbutylgroup, a 2-methylbutylgroup, ann-hexylgroup,
a 2-methylpentyl group, a 4-methylpentylgroup, a 4-methyl-2-pentyl
25 group, a 1,2-dimethylbutyl group, a 2,3-dimethylbutyl group, a
2-ethylbutyl group, an n-heptyl group, a 3-methylhexyl group, a
5-methylhexyl group, a 2,4-dimethyl pentyl group, an n-octyl group,
a t e r t - o c t y l group, a 2-ethylhexyl group, a 2-propylpentyl group,
and a 2,5-dimethylhexyl group, as a substituent group; an ethynyl
group having an unsubstituted phenyl group as a substituent group;
and an ethynylgroup having a phenylgroup, which is s u b s t i t u t e d w i t h
5 a s t r a i g h t or branched alkyl group, such as a 2-methylphenyl group,
a 4-methylphenyl group, a 3-ethylphenyl group, a 4-n-propylphenyl
group, a 4-n-butylphenyl group, a 4-isobutylphenyl group, a
4-tert-butylphenyl group, a 4-n-pentylphenyl group, a
4-tert-pentylphenyl group, a 4-n-hexylphenyl group, a
10 4-n-octylphenylgroup, anda 4-n-nonylphenylgroup, as a substituent
group.
Amongthese, anethynylgrouphavinga s t r a i g h t o r b r a n c h e d a l k y l
group such a s a methyl group, an e t h y l group, an n-propyl group, an
isopropyl group, an n-butyl group, an isobutyl group, a t e r t - b u t y l
15 group, an n-pentyl group, an isopentyl group, an n-hexyl group, a
1,2-dimethylbutyl group, a 2-ethylbutyl group, an n-heptyl group,
and an n-octyl group, as a substituent group; an ethynyl group having
a phenyl group a s a substituent group; and an ethynyl group having
aphenylgroup, which is s u b s t i t u t e d w i t h a s t r a i g h t o r b r a n c h e d a l k y l
20 group, s u c h ~ ~ aa s2 -methylphenyl group, a 4-methylphenyl group, a
3-ethylphenyl group, a 4-n-propylphenyl group, a 4-n-butylphenyl
group, a 4-isobutylphenyl group, a 4-tert-butylphenyl group, a
4-n-pentylphenyl group, and a 4-tert-pentylphenyl group as a
s u b s t i t u e n t group, a r e more p r e f e r a b l e .
25 [0025]
In a case where R1 t o Rq a r e s t r a i g h t or branched a l k y l groups,
examples of the s t r a i g h t or branched alkyl group include a methyl
.- group, an ethyl group, an n-propyl group, an isopropyl group, an
n-butyl group, an isobutyl group, a t e r t - b u t y l group, an n-pentyl
group, an isopentyl group, an neopentyl group, a tert-pentylgroup,
a 1,2-dimethylpropyl group, a 1-methylbutyl group, a 2-methylbutyl
5 group, an n-hexyl group, a 2-methylpentyl group, a 4-methylpentyl
group, a 4-methyl-2-pentyl group, a 1,2-dimethylbutyl group, a
2,3-dimethylbutyl group, a 2-ethylbutyl group, an n-heptyl group,
a 3-methylhexyl group, a 5-methylhexyl group, a 2,4-dimethyl pentyl
group, an n-octyl group, a t e r t - o c t y l group, a 2-ethylhexyl group,
10 a 2-propylpentyl group, and a 2,5-dimethylhexyl group.
Among these, a methyl group, an e t h y l group, an n-propyl group,
an isopropyl group, an n-butyl group, an isobutyl group, a t e r t - b u t y l
group, an n-pentyl group, an isopentyl group, an neopentyl group,
a 1'2-dimethylpropyl group, a 1-methylbutyl group, ann-hexyl group,
15 a 1,2-dimethylbutyl group, a 2-ethylbutylgroup, an n-heptylgroup,
ann-octylgroup, anda2-ethylhexylgrouparepreferable, andamethyl
group, an ethyl group, an n-propyl group, an isopropyl group, an
n-butyl group, an isobutyl group, a t e r t - b u t y l group, an n-pentyl
group, an isopentyl group, an n-hexyl group, a l,2-dimethylbutyl
20 group, a 2-ethylbut.yl group, an n-heptyl group, and an n-octyl group
a r e more preferable.
Such a porphyrin-based compound used i n the o p t i c a l material
of the present embodiment can improve v i s i b i l i t y of an object i n
darkness and does not a f f e c t o p t i c a l properties such as a r e f r a c t i v e
25 index or an Abbe number.
100261
The porphyrin-based compound used i n the o p t i c a l material of
the present embodiment can be produced in consideration of a ~.
well-known method itself. That is, the compound represented by
General Formula (A) can be produced by, for example, synthesizing
a compound represented by General Formula (B-1) to General Formula
5 (B-4) and a compound represented by General Formula (C-1) to General
Formula (C-4) through a dehydration condensation reaction and an
oxidation reaction (for example,
2,3-dichloro-5,6-dicyano-l,4-benzoquinon, which is a so-called
Rothermund reaction, using an acid catalyst (for example, propionic
10 acid, a boron trifluoride-ethyl ether complex, and trifluoroacetic
acid), andby reactingthe synthesizedcompoundwithmetalor ametal
salt (for example, an acetylacetonate complex, or metal acetate) in
an suitable solvent as desired.
[ 0 0 2 7 ]
15
( c-1) ( C-2 1 ( c-3 ( c-4 1
[0028]
In the formula, XI to Xg and R1 to Rq have the same meanings as
in the case of General Formula (A).
In the present specification, the porphyrin-based compound
20 represented by General Formula (A) actually represents a mixture
consisting of one or two or more kinds of isomers. Even when
describing a structure of such a mixture consisting of a plurality
of isomers, in the present specification, one structural formula
represented by General Formula (A) is described for convenience, for
example.
5 [0029]
In the optical material of the present embodiment, as the
porphyrin-based compound according to the present embodiment, it is
possible to use the mixture consisting of one or two or more kinds
of isomers. In addition, it is possible to use one kind of compound
10 withinanisomerbyseparatingtheisomersfromthemixtureasdesired.
Furthermore, it is possible to use the plurality of isomers formed
at arbitrary proportions, in combination. The porphyrin-based
compound according to the present embodiment naturally includes
crystals and also includes an amorphous.
15 [0030]
The optical material of the present embodiment includes the
characteristics of (1) to (4) which is required for a transmittance
curve measured at a thickness of 2 mm of the optical material, and
preferably further includes the characteristic of (5). The optical
20 material of .the present embodiment preferably contains
porphyrin-based compounds as organic dyes. Specifically, the
optical material ofthe present embodiment has an absorptionmaximum
wavelength in a wavelength region between wavelengths of 471 nm to
490 nm, and in detail, contains at least one kind of porphyrin-based
25 compound in which an absorption peak is in a wavelength range of 471
nm to 490 nm and the half-value width of the absorption peak is 10
nm or more and less than 50 nm, in an absorption spectrum which is
measured at an optical path length of 10 mm of a chloroform solution
thereof at a concentration of 0.01 g/L.
In the optical material of the present embodiment, one kind of
the porphyrin-based compound may be used singly or two or more kinds
5 of the porphyrin-based compounds may be used in combination.
[0031]
The half-value width in the present specification indicates a
full width at half maximum and is represented by a distance (nm)
between two intersections which are formed by the peak and a straight
10 l i n e p a r a l l e l t o a h o r i z o n t a l a x i s ~ ~ r h i c h i s d r a w n b y a v a l u e o f o n e - h a l f
of an absorption coefficient value (cg) in an absorption maximum
wavelength in the absorption spectrum.
[0032]
[Composition for Optical Material]
15 Next, a composition for an optical material of the present
embodiment will be described in detail.
The composition for an optical material of the present
embodimentcontainsaresinforanopticalmaterialoraresinmonomer;
and at least one kind of organic dyes in which an absorption peak
20 is in a wavelength range of 471 nm to 490 nm and the half-value width
of the absorption peak is 10 nm or more and less than 50 nm, in an
absorption spectrum which is measured at an optical path length of
10 mm of a chloroform solution thereof at a concentration of 0.01
g/L.
25 The organic dyes can be contained at an amount of 0.0005 parts
byweightto0.0lpartsbyweightandpreferably0.0005partsbyweight
to 0.005 parts by weight with respect to 100 parts by weight in total
of the resin for an-optical material or the resin monomer;
By containing the above-described amount of the organic dyes,
it is possible to satisfy the above-described characteristics (1)
to (4) and preferably satisfy the characteristic (5), and therefore,
5 it is possible to suitably obtain the optical material.
As these organic dyes, it is possible to use at least one kind
of compound selected fromthe porphyrin-based compounds represented
by General Formula (A). Furthermore, a resin modifier or the like
may be contained as another component.
10 First, the resin for an optical material or the resin for an
optical material which is obtained from the resin monomer will be
described.
In the present embodiment, it is possible to use the resin for
an optical material without any restrictions as long as the resin
15 for an optical material is a transparent resin.
LO0331
Examples of the transparent resin include polyurethane,
polythiourethane, polysulfide, polycarbonate, poly(meth)acrylate,
polyolefin, cyclic polyolefin, polyallyl, polyurethane urea, a
20 polyene-polyt.hio1 polymer, a ring-opening metathesis polymer,
polyester, and an epoxy resin, and it is preferable to use at least
one kind selected frompolyurethane, polythiourethane, polysulfide,
polycarbonate, poly(meth)acrylate, andpolyolefin. Thesematerials
are materials having high transparency and can be suitably used for
25 an optical material.
These materials may be used singly or as a composite material.
Polyurethane is comprised of a constituent unit -derived from
apolyisocyanate compound andaconstituentunitderivedfromapolyol
compound. Polythiourethane is comprised of a constituent unit
derivedfromapolyisocyanate compoundanda constituent unit derived
5 from a polythiol compound.
[00351
Examples of the polyisocyanate compound include aliphatic
polyisocyanate compounds such as 1,6-hexamethylene diisocyanate,
1,5-pentamethylene diisocyanate, 2,2,4-trimethylhexane
10 diisocyanate, 2,4,4-trimethylhexamethylene diisocyanate, lysine
diisocyanatomethyl ester, lysine triisocyanate, rn-xylylene
diisocyanate, a,a,a1,a'-tetramethylxylylene diisocyanate,
bis(isocyanatomethyl)naphthalene, mesitylene triisocyanate,
bis (isocyanatomethyl) sulfide, bis (isocyanatoethyl) sulfide,
15 bis(isocyanatomethyl)disulfide, bis(isocyanatoethyl)disulfide,
bis(isocyanatomethylthio)methane, bis(isocyanatoethylthio)methane,
bis (isocyanatoethylthio)e thane, and
bis(isocyanatomethy1thio)ethane;
alicyclic polyisocyanate compounds such as isophorone diisocyanate,
20 1,3-bis (isocyanatomethyl) cyclohexane,
1,4-bis(isocyanatomethyl)cyclohexane,
dicyclohexylmethane-2,2'-diisocyanate,
dicyclohexylmethane-2,4'-diisocyanate,
dicyclohexylmethane-4,4'-diisocyanate, cyclohexane diisocyanate,
25 methylcyclohexane diisocyanate, dicyclohexyl dimethylmethane
isocyanate, 2,5-bis(isocyanatomethyl)bicyclo-[2.2.1]-heptane,
2,6-bis(isocyanatomethyl)bicyclo-[2.2,l]-heptane,
3,8-bis(isocyanatomethyl)tricyclodecane,
3,9-bis(isocyanatomethyl)tricyclodecane,
4,8-bis(isocyanatomethyl)tricyclodecane, and
4,9-bis(isocyanatomethyl)tricyclodecane;
5 aromaticpolyisocyanate compounds such as naphthalene diisocyanate,
m-phenylene diisocyanate, p-phenylene diisocyanate, 2,4-tolylene
diisocyanate, 2,6-tolylene diisocyanate, biphenyl diisocyanate,
diphenylmethane-2,2'-diisocyanate,
diphenylmethane-2,4'-diisocyanate,
10 diphenylmethane-4,4'-diisocyanate, benzene triisocyanate, and
diphenylsulfide-4'4-diisocyanate; and
heterocyclic polyisocyanate compounds such as
2,5-diisocyanatothiophene, 2'5-bis(isocyanatomethyl)thiophene,
2,5-diisocyanatotetrahydrothiophene,
15 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
20 4,5-bis (isocyanatomeehyl) -1,3-dithiolane, and it is possible to use
at least one kind selected therefrom.
[0036]
Thepolyolcompoundisatleastone k i n d o f a l i p h a t i c o r a l i c y c l i c
alcohol. Specific examples thereof include straight or branched
25 aliphatic alcohol, alicyclicalcohol, or alcohols whichareobtained
by adding these alcohols with ethylene oxide, propylene oxide or
r-caprolactone , and it is possible to use at least one kind selected
therefrom.
[00371
Examples of the straight or branched aliphatic alcohol include
ethylene glycol, diethylene glycol, triethylene glycol, propylene
5 glycol, dipropylene glycol, tripropylene glycol, 1,3-propanediol,
2,2-dimethyl-1,3-propanediol, 2,2-diethyl-l,3-propanediol,
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,
10 3-methyl-l,5-pentanediol, 1,6-hexanediol, 2,5-hexanediol, glycerol,
diglycerol, polyglycerol, trimethylolpropane, pentaerythritol, and
di(trimethylolpropane), and it is possible to use at least one kind
selected therefrom.
LO038 ]
15 Examples ofthe alicyclic alcohol include 1,2-cyclopentanediol,
l,3-cyclopentanediol, 3-methyl-l,2-cyclopentanediol,
1,2-cyclohexanediol, 1,3-cyclohexanediol, 1,4-cyclohexanediol,
4,4'-bicyclohexanol, and 1,4-cyclohexane dimethanol, and it is
possible to use at least one kind selected therefrom.
20 [0039]
It is possible to use the compounds which are obtained by adding
t h e s e a l c o h o l s ~ ~ ~ i t h e t h y l e n e o x ipdreo,p yleneoxideore-caprolactone.
Examples thereof include an ethylene oxide adduct of glycerol,
ethylene oxide adduct of trimethylolpropane, ethylene oxide adduct
25 of pentaerythritol, propylene oxide adduct of glycerol, propylene
oxide adduct of trimethylolpropane, propylene oxide adduct of
pentaerythritol, caprolactone-modified glycerol,
capuolactone-modified trimethylolpropane, and
caprolactone-modified pentaerythritol.
[0040]
Examples of the polythiol compound include aliphatic polythiol
5 compounds such as methanedithiol, 1,2-ethanedithiol, 1,2,3-propane
trithiol, 1,2-cyclohexane dithiol, bis(2-mercaptoethyl)ether,
tetrakis(mercaptomethyl)methane, diethylene glycol
bis(2-mercaptoacetate), diethylene glycol
bis(3-mercaptopropionate), ethylene glycolbis(2-mercaptoacetate),
10 ethylene glycol bis(3-mercaptopropionate), trimethylolpropane
tris(2-mercaptoacetate), trimethylolpropane
tris(3-mercaptopropionate), trimethylolethane
tris(2-mercaptoacetate), trimethylolethane
tris(3-mercaptopropionate), pentaerythritol
15 tetrakis(2-mercaptoacetate), pentaerythritol
tetrakis(3-mercaptopropionate), bis(mercaptomethyl)sulfide,
bis(mercaptomethyl)disulfide, bis(mercaptoethyl)sulfide,
bis(mercaptoethyl)disulfide, bis(mercaptopropyl)sulfide,
bis(rnercaptomethylthio)methane, bis(2-mercaptoethylthio)methane,
20 bis(3-mercaptopropylthio)methane,
1,2-bis (mercaptomethylthio)e thane,
1,2-bis(2-mercaptoethylthio)ethane,
1,2-bis(3-mercaptopropylthio)ethane,
1,2,3-tris (rnercaptomethylthio) propane,
25 1,2,3-tris(2-mercaptoethylthio)propane,
1,2,3-tris(3-mercaptopropylthio)propane,
5,7-dimercaptomethyl-1,ll-dimercapto-3,6,9-trithiaundecane,
4,7-dimercaptomethyl-l,ll-dimercapto-3,6,9-trithiaundecane,
4,8-dimercaptomethyl-l,ll-dimercapto-3,6,9-trithiaundecane,
tetrakis(mercaptomethylthiomethyl)methane,
5 tetrakis(2-mercaptoethylthiomethyl)methane,
tetrakis(3-mercaptopropylthiomethyl)methane,
bis(2,3-dimercaptopropyl)sulfide,
2,5-dimercaptomethyl-1,4-dithiane, 2,s-dimercapto-1,4-dithiane,
2,5-dimercaptomethyl-2,5-dimethyl-1,4-dithiane, and esters of
10 these thioglycolic acid and mercaptopropionic acid, hydroxymethyl
sulfide bis(2-mercaptoacetate), hydroxymethyl sulfide
bis(3-mercaptopropionate), hydroxyethyl sulfide
bis(2-mercaptoacetate), hydroxyethyl sulfide
bis(3-mercaptopropionate), hydroxymethyl disulfide
15 bis(2-mercaptoacetate), hydroxymethyl disulfide
bis(3-mercaptopropionate), hydroxyethyl disulfide
bis(2-mercaptoacetate), hydroxyethyl disulfide bis(3-mercapto
propionate), 2-mercaptoethyl ether bis(2-mercaptoacetate),
2-mercaptoethyl ether bis(3-mercaptopropionate),
20 bis(2-mercaptoethyl ester)thiodiglycolate, bis(2-mercaptoethyl
ester)thiodipropionate, bis(2-mercaptoethyl
ester)dithiodiglycolate, bis(2-mercaptoethyl
ester)dithiodipropionate,
1,1,3,3-tetrakis(mercaptomethylthio)propane,
25 1,1,2,2-tetrakis (mercaptomethylthio) ethane,
tris(mercaptomethylthio)methane, and
aromatic polythiol compounds such as 1,2-dimercaptobenzene,
1,3-dimercaptobenzene, 1,4-dimercaptobenzene,
1,2-bis (mercaptomethyl)b enzene, 1,3-bis (mercaptomethyl)b enzene,
1,4-bis(mercaptomethyl)benzene, 1,2-bis(mercaptoethyl)benzene,
5 1,3-bis (mercaptoethyl)b enzene, 1,4-bis (mercaptoethyl)benzene,
1,3,5-trimercaptobenzene, 1,3,5-tris (mercaptomethyl) benzene,
1,3,5-tris(mercaptomethyleneoxy)benzene,
1,3,5-tris (mercaptoethyleneoxy)b enzene, 2,5-toluenedithiol,
3,4-toluenedithiol, 1,5-naphthalenedithiol, and
10 2,6-naphthalenedithiol; and
heterocyclic polythiol compounds such as
2-methylamino-4,6-dithiol-sym-triazine, 3,4-thiophenedithiol,
bismuthiol, 2,5-bis(mercaptomethy1)-l,4-dithiane,
4,6-bis (mercaptomethylthio) -1,3-dithiane, and
15 2-(2,2-bis(mercaptomethylthio)ethyl)-l,3-dithietane, and it is
possible to use at least one kind selected therefrom.
[00411
In the present embodiment, it is preferable to use
polythiourethane as atransparent resin. Moreover, the composition
20 foranopticaLmaterialpreferablyc~ntainsapolyisocyanatecompound
and a polythiolcompound fromthe viewpoint of improving visibility
of an object in darkness.
Among the above, as the polyisocyanate compound, it is
preferable to use at least one kind selected from
25 2,5-bis (isocyanatomethyl) -bicycle- c2.2.11 -heptane,
2,6-bis(isocyanatomethyl)-bicyclo-[2.2.1l-heptane, m-xylylene
diisocyanate, dicyclohexylmethane diisocyanate,
1,3-bis (isocyanatomethyl)c yclohexane,
I,$-bis(isocyanatomethyl)cyclohexane, isophorone diisocyanate,
1,6-hexamethylene diisocyanate, and 1,5-pentamethylene
diisocyanate.
5 It is more preferable to use at least one kind selected from
2,5-bis(isocyanatomethyl)bicyclo-[2.2.1]-heptane,
2,6-bis(isocyanatomethyl)bicyclo-[2.2.1]-heptane, m-xylylene
diisocyanate, dicyclohexylmethane diisocyanate,
1,3-bis(isocyanatomethyl)cyclohexane,
10 1,4-bis(isocyanatomethyl)cyclohexane, andisophorone diisocyanate.
[0042]
Among the above, as the polythiol compound, it is preferable
to use at least one kind selected from
4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane,
15 5,7-dimercaptomethyl-l,ll-dimercapto-3,6,9-trithiaundecane,
4,7-dimercaptomethyl-l,ll-dimercapto-3,6,9-trithiaundecane,
4,8-dimercaptomethyl-l,ll-dimercapto-3,6,9-trithiaundecane,
pentaerythritol tetrakis(3-mercaptopropionate),
bis(mercaptoethyl)sulfide, pentaerythritol
20 tetrakis(2-mercaptoaeetate), 2,5-bis(mercaptomethy1)-1,4-dithiane,
1,1,3,3-tetrakis (mercaptomethylthio)p ropane,
4,6-bis (mercaptomethylthio) -1,3-dithiane, and
2- (2,2-bis (mercaptomethylthio)e thyl) -1,3-dithietane.
It is more preferable to use at least one selected from
25 4-mercaptomethyl-l,8-dimercapto-3,6-dithiaoctane,
5,7-dimercaptomethyl-l,ll-dimercapto-3,6,9-trithiaundecane,
4,7-dimercaptomethyl-l,ll-dimercapto-3,6,9-trithiaundecane,
4,8-dimercaptomethyl-l,1l-dimercapto-3,6,9-trithiaundecane, and
pentaerythritol tetrakis(3-mercaptopropionate) .
From the viewpoint of the effect of the invention, it is more
preferable that a combination of m-xylylene diisocyanate and
5 4-mercaptomethyl-l,8-dimercapto-3,Gdithiaoctane is not contained
in the combination of the polyisocyanate compound and the polythiol
compound. In this case, a case in which m-xylylene diisocyanaie,
and 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane and another
polyisocyanate compound and/or another polythiol compound are used
10 in combination is not excluded.
[0043]
As the combination of the polyisocyanate compound and the
polythio1 compound in the present invention, the following
combination is more preferable.
15 (1) A combination of at least one kind selected from
2,5-bis (isocyanatomethyl) bicyclo- [2.2.11 -heptane,
2,6-bis(isocyanatomethyl)bicyclo-[2.2.1]-heptane, pentaerythritol
tetrakis (3-mercaptopropionate) , and
4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane
20 (2) A combination of m-xylylene diisocyanate and pentaerythritol
tetrakis(3-mercaptopropionate)
(3) A combination of at least one selected from
2,5-bis(isocyanatomethy1)bicyclo-[2.2,1]-hen and
2,6-bis(isocyanatomethyl)bicyclo-[2.2.1l-heptane, pentaerythritol
25 tetrakis(3-mercaptopropionate), and at least one selected from
5,7-dimercaptomethyl-l,1l-dimercapto-3,6,9-trithiaundecane,
4,7-dimercapiomethyl-l,ll-dimercapto-3,6,9-trithiaundecane, and
4,8-dimercaptomethyl-l,ll-dimercapto-3,6,9-trithiaundecane
( 4 ) A combination of m-xylylene diisocyanate and at least one
selected from
5,7-dimercaptomethyl-l,ll-dimercapto-3,6,9-trithiaundecane,
5 4,7-dimercaptomethyl-l,ll-dimercapto-3,6,9-trithiaundecane, and
4,8-dimercaptomethyl-l,ll-dimercapto-3,6,9-trithiaundecane
[00441
Examples of an arbitrary additive include a polymerization
catalyst, an internal release agent, a bluing agent, and an
10 ultraviolet absorber. In the present embodiment, when obtaining
polyurethane and polythiourethane, a polymerization catalyst may or
may not be used.
Examples oftheinternalreleaseagentincludeacidicphosphoric
acid ester. Examples of acidic phosphoric acid ester include
15 phosphoricmonoesterandphosphodiester, andthesecanbeusedsingly
orincombinationoftwoormorekindsthereof. Examplesofthebluing
agent include a bluing agent which has an absorption band between
anorangewavelengthregionandayellowwavelengthregioninavisible
light region and has a function of adjusting the color phase of an
20 opticalmateriaLcomprisedofaresin. Morespecifically, thebluing
agent contains a substance exhibiting ablue color to aviolet color.
[0045]
Examples of the ultraviolet absorber to be used include
benzophenone-based ultraviolet absorbers such as
25 2,2'-dihydroxy-4-methoxybenzophenone, 2-hydroxy-4-acryloyloxy
benzophenone, 2-hydroxy-4-acryloyloxy-5-tert-butylbenzophenone,
and 2-hydroxy-4-acryloyloxy-2',4'-dichlorobenzophenone;
triazine-based ultraviolet absorbers such as
2-[4-[(2-hydroxy-3-dodecyloxypropyl)oxy]-2-hydroxyphenyl]4,6-bis
(2,4-dimethylphenyl)- 1,3,5-triazine,
2-[4-(2-hydroxy-3-tridecyloxypropyl)oxy]-2-hydroxyphenyl]-4,6-bi
5 s (2,4-dimethylphenyl) -l,3,5-triazine,
2-[4-[ (2-hydroxy-3-(2'-ethyl)hexyl)oxy~-2-hydroxyphenyl]-4,6-bis
(2,4-dimethylphenyl) -1,3,5-triazine,
2,4-bis(2-hydroxy-4-butyloxyphenyl)-6-(2,4-bis-butyloxyphenyl)-l
,3,5-triazine, and 2-(2-hydroxy-4-[l-octyloxycarbonyl
10 ethoxylphenyl) -4,6-bis (4-phenylphenyl) -l,3,5-triazine;
benzotriazole-based ultraviolet absorbers such as
2-(2H-benzotriazole-2-y1)-4-methylphenol,
2-(2H-benzotriazole-2-y1)-4-tert-octylphenol,
2-(2H-benzotriazole-2-yl)-4,6-bis(l-methyl-l-phenylethyl)phenol,
15 2-(2H-benzotriazole-2-yl)-4,6-di-tert-pentylphenol,
2-(5-chloro-2H-benzotriazole-2-yl)-4-methyl-6-tert-butylphenol,
2-(5-chloro-2H-benzotriazole-2-yl)-2,4-tert-butylphenol, and
2,2'-methylenebis [6- (2H-benzotriazole-2-yl) -4- (1,1,3,3-tetrameth
ylbutyl)phenol], and preferred examples thereof include a
20 benzotriazole-based ultraviolet absorber such as
2-(2H-benzotriazole-2-y1)-4-tert-octylpheno or
2-(5-chloro-2H-benzotriazole-2-yl)-4-methyl-6-tert-butylphenol.
These ultraviolet absorbers can be used singly or in combination of
two or more kinds thereof.
25 [0046]
Polysulfide can be obtained by a method through ring-opening
polymerization of a polyepithio compound or a polythietane compound
which is a resin monomer. The composition for an optical material
can contain a resin monomer constituting these resins.
[a0471
Examples of the polyepithio compound include epithioethylthio
5 compounds such as bis(l,2-epithioethyl)sulfide,
bis [4- (epithioethylthio) phenyl] sulfide, and
bis [4- (epithioethylthio) phenyllmethane;
10 chain aliphatic 2,3-epithiopropylthio compounds such as
bis (2,3-epithiopropyl) sulfide, bis (2,3-epithiopropyl) disulfide,
1,2-bis (2,3-epithiopropylthio)p ropane,
15 1,3-bis( 2,3-epithiopropylthio)p ropane,
1,4-bis (2,3-epithiopropylthio)b utane,
20 l,5-bis (2,3-epithiopropylthio)p entane,
yl) propane,
2,2-bis(2,3-epithiopropylthiomethyl)-l-(2,3-epithiopropylthio)bu
tane,
1,5-bis(2,3-epithiopropylthio)-2-(2,3-epithiopropylthiomethyl)-3
5 -thiapentane,
l,5-bis (2,3-epithiopropylthio) -2,4-bis (2,3-epithiopropylthiometh
y1)-3-thiapentane,
1-(2,3-epithiopropylthio)-2,2-bis(2,3-epithiopropylthiomethyl)-4
-thiahexane,
10 1,5,6-tris(2,3-epithiopropylthio)-4-(2,3-epithiopropylthiomethyl
)-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
15 yl) -3,6-dithiaoctane,
l,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-epithiopropylthio
methyl) -3,6-dithiaoctane,
20 1,8-bis (2, 3-epithiopropylthio) -2,4,5-tris (2,3-epithiopropylthiom
ethyl) -3,6-dithiaoctane,
l,l, 1-tris [ [2- (2,3-epithiopropylthio) ethyl] thiomethyl] -2- (2,3-ep
ithiopropylthio)ethane,
25 ne,
1,ll-bis(2,3-epithiopropylthio)-4,8-bis(2,3-~pithiopropylthi~met
hyl) -3,6,9-trithiaundecane,
1,ll-bis (2,3-epithiopropylthio) -4,7-bis (2,3-epithiopropylthiomet
hyl) -3,6,9-trithiaundecane, and
1,ll-bis(2,3-epithiopropylthio)-5,7-bis(2,3-epithiopropylthiomet
hyl) -3,6,9-trithiaundecane;
5 cycloaliphatic 2,3-epithiopropylthio compounds such as
1,3-bis(2,3-epithiopropylthio)cyclohexane,
1,4-bis(2,3-epithiopropylthio)cyclohexane,
1,3-bis (2,3-epithiopropylthiomethyl)c yclohexane,
1,4-bis(2,3-epithiopropylthiomethyl)cyclohexane,
10 2,5-bis(2,3-epithiopropylthiomethyl)-l,4-dithiane,
2,s-bis [ [2- (2,3-epithiopropylthio)e thyl] thiomethyl]- 1,4-dithiane,
and
2,5-bis(2,3-epithiopropylthiomethyl)-2,5-dimethyl-l,4-dithiane;
aromatic 2,3-epithiopropylthio compounds such as
15 1,2-bis (2,3-epithiopropylthio)b enzene,
1,3-bis (2,3-epithiopropylthio)b enzene,
1'4-bis(2,3-epithiopropylthio)benzene,
1,2-bis(2,3-epithiopropylthiomethyl)benzene,
1,3-bis(2,3-epithiopropylthiomethyl)benzene,
20 l,4-bis (2,3-epi*hioprepylthiomethyl) benzene,
bis[4-(2,3-epithiopropylthio)phenylln~ethane,
2,2-bis[4-(2,3-epithiopropylthio)phenyl]propane,
bis [4- (2,3-epithiopropy1thio)phenyll sulfide,
bis[4-(2,3-epithiopropylthio)phenyl]sulfone, and
25 4,4'-bis(2,3-epithiopropy1thio)biphenyl;
chain aliphatic 2,3-epithiopropyloxy compounds such as
bis (2,3-epithiopropyl) ether, bis (2,3-epithiopropyloxy)methane,
1,2-bis(2,3-epithiopropyloxy)ethane,
1,2-bis (2,3-epithiopropyloxy)pcopane,
1,3-bis (2,3-epithiopropyloxy)propane,
1,3-bis(2,3-epithiopropyloxy)-2-methylpropane,
5 l,4-bis (2,3-epithiopropyloxy)b utane,
1,4-bis(2,3-epithiopropyloxy)-2-methylbutane,
1,3-bis (2,3-epithiopropyloxy)b utane,
1,5-bis(2,3-epithiopropyloxy)pentane,
1,5-bis (2,3-epithiopropyloxy)- 2-methylpentane,
10 1,5-bis(2,3-epithiopropy1oxy)-3-thiapentane,
1,6-bis (2,3-epithiopropyloxy)h exane,
1,6-bis(2,3-epithiopropy1oxy)-2-methylhexane,
1,8-bis (2,3-epithiopropyloxy)- 3,6-dithiaoctane,
1,2,3-tris (2,3-epithiopnopyloxy)propane,
15 2,2-bis(2,3-epithiopropyloxy)-1,3-bis(2,3-epithiopropyloxy
methyl)propane, 2,2-bis (2,3-epithiopropyloxy
methyl) -1- (2,3-epithiopropyloxy)b utane,
1,5-bis (2,3-epithiopropyloxy) -2- (2,3-epithiopropyloxy
methyl) -3-thiapentane,
20 1,5-bis(2,3-epit.hiopropyloxy)-2,4-bis(2,3-epithiopropyloxy
methyl) -3-thiapentane,
l-(2,3-epithiopropyloxy)-2,2-bis(2,3-epithiopropyloxy
methyl) -4-thiahexane,
1,5,6-tris (2,3-epithiopropyloxy)- 4- (2,3-epithiopropyloxy
25 methyl) -3-thiahexane,
1,8-bis(2,3-epithiopropyloxy)-4-(2,3-epithiopropyloxy
methyl) -3,6-dithiaoctane,
1,8-bis (2,3-epithiopropyloxy)- 4,5-bis (2,3-epithiopropyloxy
methyl)-3,6-dithiaoctane,
I,$-bis (2,3-epithiopropyloxy)- 4,4-bis (2,3-epithiopropyloxy
methyl) -3,6-dithiaoctane,
5 1,8-bis (2,3-epithiopropyloxy)- 2,5-bis (2,3-epithiopropyloxy
methyl) -3,6-dithiaoctane,
S,8-bis (2,3-epithiopropyloxy)- 2,4,5-tris (2,3-epithiopropyloxymet
hyl) -3,6-dithiaoctane,
1,l,1 -tris [ [2- (2,3-epithiopropyloxy)e thyl] thiomethyl] -2- (2,3-epi
10 thiopropyloxy)ethane,
l,l,2,2-tetrakis[[2-(2,3-epithiopropyloxy)ethyl]thiomethyl]ethan
e, l,ll-bis(2,3-epithiopropyloxy)-4,8-bis(2,3-epithiopropyloxy
methyl) -3,6,9-trithiaundecane,
l,ll-bis(2,3-epithiopropyloxy)-4,7-bis(2,3-epithiopropyloxy
15 methyl) -3,6,9-trithiaundecane, and
l,ll-bis(2,3-epithiopropyloxy)-5,7-bis(2,3-epithiopropyloxy
methyl) -3,6,9-trithiaundecane;
cycloaliphatic 2,3-epithiopropyloxy compounds such as
1,3-bis (2,3-epithiopropyloxy) cyclohexane,
20 l,4-bis(2,3-epithiopropyloxy)cyclohexane,
1,3-bis(2,3-epithiopropyloxy methyl)cyclohexane,
1,4-bis (2,3-epithiopropyloxy methyl) cyclohexane,
2,5-bis (2,3-epithiopropyloxy methyl) -S,4-dithiane,
2,5-bis [ [2- (2,3-epithiopropyloxy)e thyll thiomethyl]- 1,4-dithiane,
25 and 2,5-bis(2,3-epithiopropyloxy
methyl)-2,5-dimethyl-1,4-dithiane; and
aromatic 2,3-epithiopropyloxy compounds such as
1,2-bis(2,3-epithiopropyloxy)benzene,
1,3-bis (2,3-epithiopropyloxy)b enzene,
1,4-bis(2,3-epithiopropyloxy)benzene,
1,2-bis(2,3-epithiopropyloxy methyl)benzene,
5 1,3-bis(2,3-epithiopropyloxy methyl)benzene,
1,4-bis(2,3-epithiopropyloxy methyl)benzene,
bis [4- (2,3-epithiopropyloxy)p henyllmethane,
2,2-bis [4- (2,3-epithiopropyloxy)p henyl] propane,
bis [4- (2,3-epithiopropyloxy)p henyl] sulfide,
10 bis [4- (2,3-epithiopropyloxy)p henyl] sulfone, and
4,4 ' -bis (2,3-epithiopropyloxy)b iphenyl.
As the polythietane compound, it is possible to use a
metal-containing thietane compound or a non-metallic thietane
compound.
15 [0048]
These polythietane compounds contain one or more thietanyl
groups within a molecule as disclosed in W02005-95490 or Japanese
Unexamined Patent Publication No. 2003-327583. These polythietane
compounds are preferably compounds containing two or more thietanyl
20 groups in total. Examples of the compounds include sulfide-based
thietane compounds such as bisthietanyl sulfide,
bis(3-thietanylthio)disulfide, bis(3-thietanylthio)methane, and
3-( ((3'-thietanylthio)methylthio)methylthio)thietane; and
polysulfide-based thietane compounds such as
25 bis(3-thietanyl)disulfide, bis(3-thietanyl)trisulfide,
bis(3-thietanyl)tetrasulfide, and bis(3-thietany1)pentasulfide.
[0049]
Polycarbonate can be obtained through a method for reacting an
alcohol with phosgene or reacting an alcohol with chloroformate, or
by performing transesterification reaction of carbonic acid diester
compound, and it is also possible to use polycarbonate resin whlch
5 is generally available commercially. As a commercially available
product, it is possible to use Panlite Series manufactured by Teijin
Limited. The composition for an optical material of the present
embodiment can contain polycarbonate as a resin for an optical
material.
10 [0050]
Examples of poly(meth)acrylate include poly(meth)acrylate of
alkane polyols such as ethylene glycol di (meth)acrylate, propylene
glycol di (meth) acrylate, butylene glycol di (meth) acrylate,
neopentyl glycoldi(meth)acrylate, hexyleneglycoldi(meth)acrylate,
15 trimethylolpropane tri(meth)acrylate, and pentaerythritol tetra
(meth) acrylate; and
polyoxyalkanepolyol poly(meth)acrylate such as diethylene glycol
di(meth)acrylate, triethylene glycol di(meth)acrylate,
polyethylene glycol di(meth)acrylate, dipropylene glycol
20 di (meth) acrylatej polypropylene glycol di (meth) acrylate,
dibutylene glycol di(meth)acrylate, and dipentaerythritol
hexa (meth) acrylate.
The composition for an optical material of the present
embodiment can contain poly (meth) acrylate as a resin for an optical
25 material.
[0051]
Polyolefin is produced by polymerizing at least one kind of
olefin selected from a-olefins in the presence of a well-known
catalyst for olefin polymerization such as a Ziegler-Natta catalyst,
a metallocene catalyst, or a so-called post-metallocene catalyst.
a-olefin monomer may be a single component, or a composite component
5 may be copolymerized.
[0052]
When producing polyolefin, the polymerization reaction of
olefin canbeperformedthroughaliquidphasepolymerizationmethod
suchasa solutionpolymerizationmethod, asuspensionpolymerization
10 method, or a bulk polymerization method; a gas phase polymerization
method; or other well-known polymerization methods. When producing
polyolefin, liquid phase polymerizationmethods such as dissolution
polymerization and suspension polymerization (slurry
polymerization) are preferably used and a suspension polymerization
15 (slurry polymerization) method is more preferably used. Well-known
conditions can be applied to the conditions of the temperature or
the pressure for polymerization.
The composition for an optical material of the present
embodiment can containpolyolefinas a resin for an opticalmaterial.
20 100531 , r .
Cyclic polyolefin is produced by polymerizing at least one kind
of cyclic olefin selected from cyclic olefins in the presence of a
well-known olefin polymerization catalyst. The cyclic olefin
monomer may be a single component or a composite component may be
25 copolymerized. As cyclic polyolefin, APEL which is trademarked and
is manufactured by Mitsui Chemicals, Inc. can be suitably used as
it has high transparency.
roo541
Polyallylis producedbypolymerizing at least one kindof allyl
group-containing monomer selected from allyl group-containing
monomersinthepresenceofaruell-knownpolymerizationcatalyst~~ith
5 properties of generating radicals. As the allyl group-containing
monomers, it is possible to suitably use allyl diglycol carbonate
or diallylphthalate which is generally available in the market.
lo0551
Polyurethane urea is a reaction product caused by polyurethane
10 prepolymer and a diamine hardener, and a representative example
thereof is TRIVEXwhichistrademarkedavailable from PPG Industries,
Inc. Polyurethane polyurea is a material having high transparency
and can be suitably used.
[0056]
15 A polyene-polythiol polymer is a polymer product which is
generated through addition polymerization and ethylene chain
polymerization and consists of a polyene compound having two or more
ethylenic functional groups in onemolecule anda polythiolcompound
having two or more thiol groups in one molecule.
20 COO571
Examples of the polyene compound in the polyene-polythiol
polymer include anallylalcohol derivative, esters of (meth)acrylic
acid and polyhydric alcohol, urethane acrylate, and divinylbenzene.
One or two or more kinds thereof can be used. Examples of the allyl
25 alcoholderivativeincludetriallylisocyanurate, triallylcyanurate,
diallyl maleate, diallyl fumarate, diallyl adipate, diallyl
phthalate, triallyl trimellitate, tetraallyl pyromellitate,
glycerin diallyl ether, trimethylolpropane diallyl ether,
pentaerythritoldiallyl ether, andsorbitoldiallylether. Examples
of the polyhydric alcohol among esters of (meth)acrylic acid and
polyhydric alcohol include ethylene glycol, propylene glycol,
5 1,4-butanediol, 1,6-hexanediol, glycerin, trimethylolpropane,
pentaerythritol, and sorbitol.
[0058]
The ring-opening metathesis polymer is a polymer which is
obtainedbysubjectingcyclicolefinsto ring-openingpolymerization
10 using a catalyst. There is no particular restriction in the cyclic
olefinsr~hichcanbesubjectedtoring-openingpolymerizationaslong
as the olefins have a cyclic structure, but in general, examples
thereof include 3-40C monocyclic cycloalkenes, monocyclic
cycloalkadienes, polycyclic cycloalkenes, and polycyclic
15 cycloalkadienes. Specific examples of the monocyclic cycloalkenes
include cyclobutene, cyclopentene, cyclohexene, and cyclooctene.
Specific examples of the monocyclic cycloalkadienes include
cyclobutadiene, 1,3-cyclopentadiene, 1,3-cyclohexadiene,
1,4-cyclohexadiene, and 1,5-cyclooctadiene. Examples of the
20 polycyclic cycloalkenes include norbornene and
tetracyclo [6.2.1.1 3s60.~ '~]dodeca-4-ene.E xamples of the polycyclic
cycloalkadienesincludenorbornadieneanddicyclopentadiene. These
may be substituted with oxygen, sulfur, halogen, or the like.
Furthermore, these may be used by being hydrogenated. Suitable
25 examples thereof include ARTON (trademark) manufactured by JSR
Corporation.
[0059]
Polyester is subjected to condensation polymerization in the
presenceofaLewis acidcatalystrepresentedbyanantimonycompound
oragermaniumcompound, orawell-knorinpolyester-producingcatalyst
such as an organic acid and an inorganic acid. Specifically,
5 polyester refers to polyester comprised of one or two or more kinds
selected from polycarboxylic acid containing dicarboxylic acid and
an ester-forming derivative thereof and one or two or more kinds
selected from polyhydric alcohol containing glycol; polyester
comprisedofhydroxycarboxylicacidandan ester-formingderivative
10 thereof; or polyester comprised of cyclic ester.
[00601
Examples of the dicarboxylic acid include saturated aliphatic
dicarboxylicacidexemplifiedbyoxalicacid, malonicacid, succinic
acid, glutaricacid, adipicacid, pimelicacid, subericacid, azelaic
15 acid, sebacic acid, decane dicarboxylic acid, dodecane dicarboxylic
acid, tetradecane dicarboxylic acid, hexadecane dicarboxylic acid,
1,3-cyclobutane dicarboxylic acid, 1,3-cyclopentane dicarboxylic
acid, 1,2-cyclohexanedicarboxylic acid,
1,3-cyclohexanedicarboxylicacid, 1,4-cyclohexanedicarboxylic acid,
20 2,5-norbornane dicarboxylic acid, and dimer acid, or ester-forming
derivatives thereof; unsaturated aliphatic dicarboxylic acid
exemplified by fumaric acid, maleic acid, and itaconic acid, or
ester-forming derivatives thereof; and aromatic dicarboxylic acid
exemplified by orthophthalic acid, isophthalic acid, terephthalic
25 acid, 5-(alkali metal)sulfoisophthalic acid, diphenic acid,
1,3-naphthalenedicarboxylic acid, 1,4-naphthalenedicarboxylic acid,
1,5-naphthalenedicarboxyl$cacid, 2,6-naphthalenedicarboxylic acid,
2,7-naphthalenedicarboxylic acid, 4,4'-biphenyldicarboxylic acid,
4,4'-biphenyl sulfone dicarboxylic acid, 4,4'-biphenyl ether
dicarboxylic acid, 1,2-bis(phen0xy)ethane-p,p'-dicarboxylic acid,
pamoic acid, and anthracene dicarboxylic acid, or ester-forming
5 derivativesthereof. Terephthalicacidandnaphthalenedicarboxylic
acid, in particular, 2,6-naphthalenedicarboxylic acid, are
preferable among these dicarboxylic acids in terms of physical
propertiesofpolyestertobeobtained, andanotherdicarboxylicacid
may be set as a constituent component as necessary. Examples of
10 polycarboxylic acid other than these dicarboxylic acids include
ethane tricarboxylic acid, propane tricarboxylic acid, butane
tetracarboxylic acid, pyromellitic acid, trimellitic acid, trimesic
acid, and 3,4,3',4'-biphenyltetracarboxylic acid or ester-forming
derivatives thereof.
15 [0061]
Examples of glycol include aliphatic glycols exemplified by
ethylene glycol, 1,2-propylene glycol, 1,3-propylene glycol,
diethylene glycol, triethylene glycol, 1,2-butylene glycol,
1,3-butylene glycol, 2,3-butylene glycol, 1,4-butylene glycol,
20 1,5-pentanediol, neopentyl glycol, 1,6-hexanediol,
1,2-cyclohexanediol, 1,3-cyclohexanediol, l,4-cyclohexanediol,
1,2-cyclohexane dimethanol, 1,3-cyclohexane dimethanol,
1,4-cyclohexane dimethanol, 1,4-cyclohexane diethanol,
1,lO-decamethylene glycol, 1,12-dodecanediol, polyethyleneglycol,
25 polytrimethyleneglycol, andpolytetramethyleneglycol; andaromatic
glycols exemplified by hydroquinone, 4,4'-dihydroxy bisphenol,
1,4-bis(P-hydroxyethoxy)benzene, 1,4-bis(b-hydroxyethoxy
phenyl)sulfone, bis(p-hydroxyphenyl)ether,
bis (p-hydroxyphenyl) sulfone, bis (p-hydroxyphenyl)m ethane,
1,2-bis(p-hydroxyphenyl)ethane, bisphenol A, bisphenol C,
2,5-naphthalene diol, and glycols obtained by adding ethylene oxide
5 to these glycols.
[00621
Among these glycols, ethylene glycol, 1,3-propylene glycol,
1,4-butylene glycol, and 1,4-cyclohexane dimethanol are preferable.
Examples ofthe polyhydric alcohol other than these glycols include
10 trimethylol methane, trimethylol ethane, trimethylol propane,
pentaerythritol, glycerol, and hexanetriol.
[00631
As polyester, polyethylene terephthalate, polybutylene
terephthalate, polypropylene terephthalate, poly(l,4-cyclohexane
15 dimethylene terephthalate), polyethylene naphthalate, polybutylene
naphthalate, and polypropylene naphthalate, and copolymers thereof
are preferable.
[0064]
The epoxy resin is a resin which is obtained by subjecting an
20 epoxy compound to ring-opening polymerization, and examples of the
epoxy compound include phenolic epoxy compounds which are obtained
through condensation reaction between an epihalohydrin compound and
a polyhydric phenol compound such as bisphenol A glycidyl ether, or
bisphenol F glycidyl ether;
25 alcohol-based epoxy compounds which are obtained through
condensation between an epihalohydrin compound and a polyhydric
alcohol compound such as hydrogenated bisphenol A glycidyl ether,
-----hydrogenatedb isphenol F glycidyl ethe~r,o r cyclohexane dimethanol;
glycidyl ester-based epoxy compounds which are obtained through
condensation between an epihalohydrin compound and a polyvalent
organic acid compound such as
5 3,4-epoxycyclohexylmethyl-3',4'-epoxycyclohexane carboxylate or
1,2-hexahydrophthalic acid diglycidyl ester; and
amine-based epoxy compounds which are obtainedthrough condensation
between an epihalohydrin compound and primary and secondary amine
compounds. In addition, other examples thereof include a l i p h a t i c
10 polyvalent epoxy compounds such as vinylcyclohexene diepoxide such
as 4-vinyl-1-cyclohexane diepoxide.
[0065]
Thecomposition foranopticalmaterialcanbeobtainedbymixing
the above-described components through a predetermined method.
15 The order or themethod formixingcomponentsinthe composition
is not p a r t i c u l a r l y limited as long as it is possible t o evenly mix
the components with each other, and can be performed through a
well-known method. Examples of the well-known method include a
method forpreparingamasterbatch containing apredeterminedamount
20 of an additive .andsdispersing and dissolving t h i s masterbatch in a
solvent. For example, in a case of polyurethane resin, there is a
process for producing a masterbatch by dispersing and dissolving an
additive in a polyisocyanate compound.
roo661
25 Amoldedproductcontainingorganicdyes canbe obtainedthrough
a method for polymerizing the composition for an optical material
which is obtained by mixing organic dyes with a resin monomer for
- an optical material, or a method f o r curing the composition f o r an
o p t i c a l material containing organic dyes and a resin for an o p t i c a l
material.
[00671
5 [Molded Product]
Hereinafter, a molded product of the present embodiment w i l l
be described.
The molded product of the present embodiment is obtained by
polymerizing and curing the composition for an o p t i c a l material of
10 the present embodiment. The molded product contains organic dyes
and a r e s i n for an o p t i c a l material and can be used as an o p t i c a l
material. Examples of the optical material include an
a n t i - r e f l e c t i o n film used for various p l a s t i c lenses such a s p l a s t i c
spectacle lenses, goggles, v i s i o n c o r r e c t i o n spectacle lenses,
15 lenses f o r imaging equipment, Fresnel lenses f o r l i q u i d c r y s t a l
projectors, l e n t i c u l a r l e n s e s , andcontactlenses; a sealingmaterial
for a light-emitting diode (LED); an o p t i c a l waveguide; an o p t i c a l
adhesive usedin joining o p t i c a l lenses or opticalwaveguidesto each
other; an a n t i r e f l e c t i o n film used for o p t i c a l lenses; a transparent
20 coatingwhichisusedformembers ( a s u b s t r a t e , a l i g h t - g u i d i n g p l a t e ,
a film, or a sheet) f o r l i q u i d c r y s t a l display; a windscreen of a
vehicle or a windshield of a helmet of a motorbike; or a transparent
s u b s t r a t e . The molded product can be obtained fromthe composition
for an o p t i c a l material of the present embodiment. The o p t i c a l
25 material of the present embodiment can contain an u l t r a v i o l e t
absorber. P l a s t i c spectacle lenses, windscreen of a vehicle, a
windshield of a helmet of a motorbike, and the l i k e are preferable
- a s t h e optical materials.
[0068]
[Optical Material]
Next, an optical material of the present embodiment and use
5 thereof w i l l be described.
The present embodiment is characterized i n t h a t an o p t i c a l
material, i n w h i c h p u p i l l a r y l i g h t r e f l e x i s suppressedandincidence
oflightintotheeyesindarknessisassistedbyselectivelyabsorbing
only l i g h t in a wavelength range of 471 nm t o 490 nm, and therefore,
10 an object in darkness is more e a s i l y v i s i b l e , has been found.
[0069]
In general, eyes are dazzled by l i g h t from a streetlamp or from
a headlight of a vehicle a t night, and therefore, an object is barely
v i s i b l e . Furthermore, l i g h t is i r r e g u l a r l y r e f l e c t e d by a w e t road
15 surface or raindrops during r a i n f a l l , and therefore, an object
becomes even more barely v i s i b l e . This is because l i g h t having a
wavelength of 482 nm as a center a c t s on a photoreceptor within the
eyes, pupillarylightreflexisprompted, andthe pupil is contracted
t o suppress incidence of l i g h t i n t o the eyes.
20 [0070] ~ s
According t o the o p t i c a l material of the present embodiment,
pupillary l i g h t reflex is suppressed and incidence of l i g h t i n t o t h e
eyes in darkness is a s s i s t e d by selectively absorbing l i g h t having
482 nmas a center, andtherefore, a n o b j e c t i n d a r k n e s s i s m o r e e a s i l y
25 v i s i b l e .
[0071]
For example, when observing a dark place a t night through the
optical material of the present embodiment comprised of a
porphyrin-based compound represented by General Formula (A) and a
resin for an optical material, visibility is improved regardless of
the occurrence of rainfall, and therefore, it is possible to obtain
5 a good visibility.
Particularly, in the present embodiment, it is possible to
improve the rate of blocking light in a region around 440 nm to 540
nmbysatisfyingthe specifiedrequirements foratransmittancecurve,
which is preferable from the viewpoint of the above effect.
10 (00721
Representative examples of the configuration of the optical
material of the present embodiment include an optical material
comprised of a lens base material; an optical material comprised of
a lens base material and a film layer; an optical material comprised
15 of a lens base material and a coating layer; and an optical material
comprised of a lens base material, a film layer, and a coating layer.
Specific examples of the optical material of the present
embodiment include an optical material comprised of only a lens base
material; an optical material which is obtained by stacking film
20 layers over at least one surface of a lens base material; an optical
material which is obtained by stacking coating layers over at least
one surface of a lens base material; an optical material which is
obtained by stacking a film layer and a coating layer over at least
one surface of a lens base material; and an optical material which
25 is obtained by interposing a film layer between two lens base
materials.
100731
The optical material of the present embodiment has the above
c h a r a c t e r i s t i c s of (1) t o (4), and preferably further has the above
c h a r a c t e r i s t i c of ( 5 ) , as the whole optical material.
The amount of organic pigment contained in an o p t i c a l material
5 i s not p a r t i c u l a r l y limited as long as the amount of organic pigment
is within the range satisfying the above-described c h a r a c t e r i s t i c s
of a transmittance curve. In a case of using a t l e a s t one kind of
porphyrin-based compounds, the organic pigment can be contained a t
amounts of 5 ppm t o 100 ppm and preferably a t amounts of 5 ppm t o
10 50 ppm from the viewpoint: of the above-described e f f e c t .
[GO741
Forexample, amoldedproduct (alensbasematerialoranoptical
film) is prepared using a composition for an optical material
containingnoorganicdyes. Next, organicdyesaredispersedinwater
15 orasolvent,themoldedproductisimmersedintheobtaineddispersion
liquid, and the molded product is impregnated with the organic dyes
and is dried. It is possible t o prepare an optical material using
the molded product which is obtained i n t h i s manner.
[GO751
20 In addition, it is possible to impregnate t h e o p t i c a l material
with the porphyrin-basedcompound representedby General Formula (A)
a f t e r the o p t i c a l material is prepared. In addition, it is possible
t o immerse a p l a s t i c spectacle l e n s , which includes a lens base
material, and a film layer and a coating layer which are stacked as
25 necessary, in dispersion liquid containing organic dyes, and t o
impregnate the p l a s t i c spectacle lens with the organic dyes.
[GO761
The amount mf organic pigment impregnated can be controlled to
be a desired impregnation amount using the concentration of organic
pigment in dispersion l i q u i d , t h e temperature o f a dispersion liquid,
andatimeperiodforwhicharesin composition for a n o p t i c a l m a t e r i a l
5 is immersed. The impregnation amount is f u r t h e r increased as the
concentrationoforganicpigmentismadetobehigher,thetemperature
of a dispersion l i q u i d is made t o be higher, and the immersion time
is made t o be longer. In a case where it is necessary t o precisely
control the impregnation amount, the control thereof is carried out
10 byrepeatingtheimmersionpluraltimesundertheconditionofasmall
impregnation amount.
In addition, it is also possible t o form an organic
pigment-containing coating layer over an o p t i c a l material such as
a p l a s t i c lens, usinganorganicpigment-containing coatingmaterial
15 (composition for a n o p t i c a l material).
Theopticalmaterialhaving sucha configurationcanbe suitably
used as a p l a s t i c spectacle lens, and can be attached t o a windshield
of a helmet or the l i k e or a windscreen of a vehicle or the l i k e as
a sheet or a film.
20 The present invention is not limited t o the above-described
embodiment and various modes can be taken within a range i n which
t h e e f f e c t of the present invention is not impaired.
[0077]
For example, i f an o p t i c a l material can s a t i s f y the
25 above-describedcharacteristicsof (1) to ( 4 ) , andpreferablyfurther
s a t i s f y the above-described c h a r a c t e r i s t i c of ( 5 ) , it is possible
t o obtain the o p t i c a l material without using the "composition for
an optical material containing a porphyrin-based compound
representedbyGenera1 Formula (A)"oftheabove-describedembodiment.
It is possible to use the "composition for an optical material" of
the above-described embodiment except that the composition for an
5 optical material does not contain the porphyrin-based compound
represented by General Formula (A) and it is possible to employ the
same configuration.
Hereinafter, the plastic lens which is a preferred mode of an
optical material will be described in detail.
10 lo0781
[Plastic Lens]
Examples ofaplastic lens includethe following configuration.
(A) Plastic lens including lens base material comprised of
composition for optical material of present embodiment
15 (B) Plastic lens including coating layer or film comprised of
composition foropticalmaterial ofpresent embodiment, overat least
one surface of lens base material (but, excluding lens base material
obtainedfromcompositionforopticalmaterialofpresentembodiment)
(C) Plastic lens in which lens base materials (but, excluding lens
20 base materials obtained from composition for optical material of
present embodiment) are stacked over both surfaces of film comprised
of composition for optical material of present embodiment
In the present embodiment, it is possible to use these plastic
lenses suitably.
25 Hereinafter, each of the embodiments \$ill be described.
[00791
(Embodiment; A)
A process for producing a p l a s t i c lens including a lens base
material comprised of a composition for an o p t i c a l material of the
present embodiment is not p a r t i c u l a r l y limited, but preferred
examples of the production method include cast polymerization using
5 a lens casting mold. The lens base material can be comprised of
polyurethane, polythiourethane, polysulfide, poly(meth)acrylate,
and the l i k e , and it is possible t o use a composition for an optical
material of the present embodiment containing organic dyes and
monomers ( r e s i n monomer for an o p t i c a l material) of t h e s e r e s i n s .
10 [00801
Specifically, a composition for an o p t i c a l m a t e r i a l is injected
i n t o a cavity of a mold which is held by a gasket, tape, or the like.
At t h i s t i m e , in many cases, it is preferable t o perform a degassing
treatment under reduced pressure, a f i l t r a t i o n treatment under
15 pressures or reducedpressure, or the l i k e as necessaryinaccordance
with the properties required for a p l a s t i c lens t o be obtained.
[0081]
After injecting the composition i n t o the cavity thereof, the
lens casting mold is heated i n an oven, or i n a heatable device in
20 water or the l i k e using a predetermined temperature program, and the
heatedlens castingmold is curedandmolded. Aresinmoldedproduct
may be subjected t o a treatment such as annealing as necessary.
[0082]
In the present embodiment, when molding a resin, various
25 additives such as a chain extender, a cross-linking agent, a l i g h t
s t a b i l i z e r , an antioxidant, an oil-soluble dye, a f i l l e r , and an
adhesion-improving agent may be added, similarly t o a rs~ell-known
molding method depending on the purpose, in addition to the
above-described "arbitrary additive".
[00831
In addition, the plastic lens in the present embodimentmay have
5 various coating layers over a lens base material comprised of the
composition for an optical material of the present embodiment in
accordance with the purpose or use thereof. It is possible to make
the coating layers contain organic dyes. The coating layers
containing organic dyes can be prepared using a coating material
10 (composition) containing organic dyes. Alternately, the coating
layers containingorganic dyes canbe preparedby immersing aplastic
lens, to which coating layers are attached, in a dispersion liquid
which is obtained by dispersing organic dyes in water or a solvent
and impregnatingthe coating layers with the organic dyes, after the
15 coating layers are formed.
[0084]
(Embodiment : B)
A plastic lens in the present embodiment includes a layer or
a film comprised of a composition for an optical material of the
20 present embodiment over at least one surfaceofalens basematerial.
The lens base material is not comprised of the composition for an
optical material of the present embodiment.
[00851
Examples of the process for producing the plastic lens in the
25 present embodiment include (B-1) a process for producing a lens base
material, and subsequently stacking a film or a sheet comprised of
the composition for an optical material of the present embodiment
- o v e r a t l e a s t one s u r f a c e o f t h e lensbasematerial; and (B-2) amethod
for disposing a film or a sheet comprised of the composition for an
o p t i c a l material of the present embodiment along one inner wall of
a mold which is held by a gasket, tape, or the l i k e , which w i l l be
5 described l a t e r , in a cavity of the mold, and subsequently i n j e c t i n g
the composition for an o p t i c a l material into the cavity, and curing
the composition.
[00861
The f i l m o r t h e sheetcomprisedofthe composition for a n o p t i c a l
10 material of the present embodiment which is used i n the method of
(B-1) is not p a r t i c u l a r l y limited. For example, p e l l e t s of the
composition for an o p t i c a l material obtained through melting and
kneading, impregnating, or the l i k e can be obtained through various
well-known methods in the r e l a t e d a r t . Specific examples of the
15 methods include molding methods such as an injection molding method,
a p r o f i l e extrusion molding method, a pipe molding method, a tube
molding method, a coating molding method of dissimilar molded
products, an injection blow molding method, a d i r e c t blow molding
method, aT-diesheet orfilmmoldingmethod, an i n f l a t i o n filmmolding
20 method, and a press .molding method. The obtained film or sheet
contains polycarbonate, polyolefin, or the l i k e .
The l e n s b a s e m a t e r i a l canbe obtained fromawell-knormoptical
resin, and examples of t h e o p t i c a l r e s i n include (thio)urethane and
*
polysulfide.
25 A well-known method can be used as the method for stacking the
f i l m o r t h e sheetcomprisedofthecomposition f o r a n o p t i c a l m a t e r i a l
of the present embodiment on the surface of the lens base material.
Cast polymerization in the method of (B-2) can be performed
similarly t o the process of the p l a s t i c lens i n Embodiment: A, and
examples of a composition used for cast polymerization include a
5 compositioncontaininga resinmonomer f o r a n o p t i c a l m a t e r i a l (which
does not contain organic dyes).
[00881
In addition, the p l a s t i c lens in the present embodimentmayhave
various coating layers overalensbasematerialora " f i l m o r a l a y e r "
10 comprised of the composition for an o p t i c a l material i n accordance
with the purpose or use thereof. Similarly t o the p l a s t i c lens i n
Embodiment: A, it is possible t o make the coating layers contain
organic dyes.
[0089]
15 (Embodiment; C)
In a p l a s t i c l e n s i n the present embodiment, l e n s b a s e m a t e r i a l s
(excludinglens basematerials which are obtained froma composition
for an o p t i c a l material of the present embodiment) are stacked on
both surfaces of a film comprised of the composition for an o p t i c a l
20 material of the,present embodiment.
[0090]
Examples of the process for producing the p l a s t i c lens in the
present embodiment include (C-1) a process for producing lens base
materials, andsubsequentlystackingtheproducedlensbasematerials
25 on both surfaces of a f i l m or a sheet comprised of the composition
for an o p t i c a l material of the present embodiment; and (C-2) a method
for disposing a film or a sheet comprised of the composition for an 1
opticalmaterialofthepresententbodiment in a cavityofamoldwhich
is held by a gasket, tape, or t h e l i k e , i n a s t a t e of being separated
from the inner wall of the mold, and subsequently i n j e c t i n g t h e
composition for an optical material i n t o t h e cavity, and curing the
5 composition.
[0091]
As the film or the sheet comprised of the composition for an
o p t i c a l material of the present embodiment, and the lens base
materials which are used in the method of ( C - l ) , the same f i l m or
10 sheet andthe same lens basematerials as thoseinthemethod of (B-1)
of the p l a s t i c lens i n Embodiment: B can be used.
A well-known method can be used as the method f o r stacking the
f i l m o r t h e sheetcomprisedofthe composition f o r a n o p t i c a l m a t e r i a l
o f t h e present embodiment o n t h e surfaces o f t h e l e n s b a s e m a t e r i a l s .
15 Specifically, the method of (C-2) can be performed as follows.
100921
The f i l m o r t h e sheetcomprisedofthe composition for an o p t i c a l
material of the present embodiment is i n s t a l l e d i n a space of a lens
casting mold which is used f o r the process f o r producing a p l a s t i c
20 letis i n Embodiment: ,A such t h a t t h e both surfaces of the f i l m or the
sheet thereof become p a r a l l e l t o the inner surface of the mold on
an opposing front side.
[0093]
Next, a composition containing a resin monomer for an o p t i c a l
25 material (which does not contain organic dyes) is injected i n t o two
spaces between the mold and a polarization film using predetermined
i n j e c t i o n means, i n the space of the lens casting mold.
I
[00941
After injecting the composition i n t o t h e gap portions, the lens
casting mold is heated in an oven, or in a heatable device in water
or the l i k e usingapredeterminedtemperature program, andtheheated
5 lens casting mold is cured and molded. A r e s i n molded product may
be subjected to a treatment such as annealing as necessary.
[00951
Inaddition, the p l a s t i c l e n s in the present embodiment mayhave
various coating layers over a lens base material in accordance with
10 the purpose or use thereof. Similarly t o the p l a s t i c lens in
Embodiment: A, it is possible to make the coating layers contain
organic dyes.
[00961
[ P l a s t i c Spectacle Lens]
15 A p l a s t i c spectacle lens can be obtained using the p l a s t i c l e n s
o f t h e p r e s e n t embodiment. Acoating layermaybe a p p l i e d t o a single
surface or both surfaces of the p l a s t i c lens as necessary.
[00971
Specific examples of the coating layer include a primer layer,
20 a h a r d c o a t l a y e r , a n a n t i - r e f l e c t i o n l a y e r , ananti-fogcoatinglayer,
an anti-contamination layer, and a water-repellent layer. These
coating layers can be used singly or a p l u r a l i t y of coating layers
can be used by being multilayered. In a case of applying coating
l a y e r s t o b o t h surfaces o f a p l a s t i c lens, the same or d i f f e r e n t kinds
25 of the coating layers may be applied to the surfaces.
These coating layersmaybe usedtogetherwith organicdyes used
in the present embodiment; an infrared ray absorber for the purpose
of protecting the eyes from an infrared ray; a l i g h t s t a b i l i z e r o r
an antioxidant for the purpose of improving weather resistance of
a lens; dyes or pigments for the purpose of enhancing fashionability
5 of a lens; photochromic dyes or pigments; an a n t i s t a t i c agent; and
well-known additives in order t o increase the s p e c i f i c properties
o f a l e n s . Thecoatinglayerswhichareperformedthroughapplication
may contain various leveling agents f o r t h e purpose of improving
application properties may be used.
10 [0099]
In general, a primer layer is formed between a lens and a hard
coatlayertobedescribedbelow. Theprimer layer is a c o a t i n g l a y e r
which is intended t o improve adhesion between the lens and the hard
coat layer which is formed on the primer layer, and it is possible
15 t o improvetheimpact resistancedependingonthecase. As theprimer
layer, any material can be used as long as the material has high
adhesion with respect t o the obtained lens. In general, an
urethane-based resin, an epoxy-based resin, a polyester resin, a
melamine-based resin, a primer composition having polyvinyl acetal
20 asamaincomponent, o r t h e l i k e c a n b e u s e d . As theprimercomposition,
a s u i t a b l e solvent which does not a f f e c t a lens may be used f o r the
purpose of adjusting the viscosity of the composition. As a matter
of course, the primer composition may be used r.iithout any solvent.
[OlOO]
25 The primer layer can be formed through e i t h e r method o f an
applicationmethodoradrymethod. I n a c a s e o f u s i n g t h e a p p l i c a t i o n
method, a primer layer is formed by solidifying a primer composition
a f t e r applying the primer composition to a lens through a well-known
application method such as spin coating and dip coating. In a case
of performing the dry method, a primer layer is formed through a
well-known dry method such as a CVD method or a vacuum evaporation
5 method. When forming a primer layer, the surface of a lens may be
subjected t o a pretreatment such as an alkaline treatment, a plasma
treatment, a n d a n u l t r a v i o l e t treatment as necessary f o r t h e purpose
of improving adhesion.
The hard coat layer is a coating layer which is intended t o
10 providethesurfaceofalenswithfunctionssuchasscratchresistance,
abrasion resistance, moisture resistance, hot water resistance, heat
resistance, or weather resistance.
[OlOl]
The hard coat layer is generally composed of the composition
15 containing an organic s i l i c o n compound having c u r a b i l i t y , and a t
l e a s t one kind of oxide f i n e p a r t i c l e s of elements selected from an
element group consisting of Si, A l , Sn, Sb, Ta, Ce, La, Fe, Zn, W,
Z r , In, and T i and/or a t l e a s t one kind of f i n e p a r t i c l e s comprised
of a composite oxide of two or more kinds of elements selected from
20 the element ,.group.
[01021
I t i s p r e f e r a b l e t h a t t h e h a r d c o a t c o m p o s i t i o n c o n t a i n s a t l e a s t
e i t h e r of amines, amino acids, metal acetylacetonate complexes,
organicacidmetal s a l t s , perchloricacids, s a l t s o f p e r c h l o r i c a c i d s ,
25 acids, metal chlorides, and polyfunctional epoxy compounds, in
addition t o the above-described components. As the hard coat
composition, a s u i t a b l e solvent which does not a f f e c t a lens may be
used, or the hard coat composition may be used without any solvent.
[0103]
The hard coat layer is formed by being cured a f t e r applying a
hard coat composition to the hard coat layer through a well-known
5 application method such as spin coating and dip coating. Examples
of the curing method include a heat curing method, a curing method
performed through energy ray i r r a d i a t i o n such a s u l t r a v i o l e t rays
and v i s i b l e rays, and the l i k e . In order t o suppress generation of
interference fringes, the difference between t h e r e f r a c t i v e index
10 of the hard coat layer and the r e f r a c t i v e index of the lens is
preferably within a range of f 0.1.
[0104]
In general, an a n t i - r e f l e c t i o n l a y e r is formed on the hard coat
layer as necessary. There is an inorganic anti-reflection layer and
15 an organic a n t i - r e f l e c t i o n l a y e r . In a case of the inorganic
a n t i - r e f l e c t i o n layer, an a n t i - r e f l e c t i o n l a y e r is formed through
adrymethodsuchasavacuumevaporationmethod, a sputteringmethod,
an ion plating method, an ion beam-assisting method, and a CVD method
usinganinorganicoxidesuchasSi0~andTiO~.I n a c a s e o f t h e o r g a n i c
20 a n t i - r e f l e c t i o n . l a y e r , an a n t i - r e f l e c t i o n l a y e r is formed through
a wet method using a composition containing an organic s i l i c o n
compound and silica-based f i n e p a r t i c l e s having an i n t e r n a l c a v i t y .
[01051
There is an a n t i - r e f l e c t i o n monolayer and an a n t i - r e f l e c t i o n
25 multilayer. In a case where the a n t i - r e f l e c t i o n l a y e r is used as
the monolayer, it is preferable t h a t t h e r e f r a c t i v e index of the
monolayer becomes s m a l l e r t h a n t h e r e f r a c t i v e index o f t h e hard coat
layer by at-least 0.1 or more. In order to effectively exhibit the
anti-reflection function, an anti-reflection multilayer film is
preferable. In this case, low refractive index films and high
refractive index films are alternately stacked. Even in this case,
5 it is preferable that the difference in the refractive index between
a low refractive index film and a high refractive index film is 0.1
or more. Examples of the high refractive index film include a ZnO
film, a Ti02 film, a CeOz film, a Sb205 film, a SnOz film, a Zr02 film,
and a Ta205 film. Examples of the low refractive index film include
10 a Si02 film or the like.
[0106]
An anti-fog layer, an anti-contamination layer, and a
water-repellent layer may be formed on the anti-reflection layer as
necessary. The treatment method, the treatment material, and the
15 like of the method for forming the anti-fog layer, the
anti-contamination layer, and the water-repellent layer are not
particularly limited as long as these do not adversely affect the
anti-reflection function, and it is possible to use an anti-fog
treatment method, an anti-contamination treatment method, a
20 water-repellent~~~kreatmentmethoadn,d amaterial whicharewell known.
Examples ofthe anti-fog treatmentmethod and the anti-contamination
treatment method include a method for covering the surface of an
anti-reflection layer with a surfactant; a method for making the
surface thereof have water absorbing properties by providing a
25 hydrophilic film; a method for improving water absorbing properties
by covering the surface thereof with fine recesses and projections;
a method for making the surface thereof have water absorbing
properties using an photocatalytic activity;-and a method for
preventing adhesion of water droplets by subjecting the surface
thereof to a In addition, examples
of the water-repellent treatment method include a method for forming
5 a water-repellent treatment layer through evaporating or sputtering
of a fluorine-containing silane compound; or a method for forming
a water-repellent treatment layer by dissolving a
fluorine-containing silane compound in a solvent and subsequently
coating the surface thereof with the dissolved fluorine-containing
10 silane compound.
[Examples]
[0107]
Hereinafter, the present invention will be described in detail
using Examples, but is not limited thereto. The material and the
15 evaluation method used in Examples of the present invention are as
follows.
[0108]
[Measurement Method of Transmittance Curve]
A Shimadzu spectrophotometer UV-1600 manufactured by Shimadzu
20 Corporation was used as a measurement device, and an
ultraviolet-visible light spectrum was measured using a plano lens
with a thickness of 2 mm.
[01091
[Visibility Evaluation of Sample Lens]
2 5 A produced sample lens was shaved off in a suitable shape using
an edging machine manufactured by Nidek Co., Ltd. and a spectacle
frame was installed to produce sample spectacles.
-- V i s i b i l i t y of an object a t night was evaluated a f t e r i n s t a l l i n g
the sample spectacles. The evaluation was performed by five people
designatedbyAtoEandriasperformedinaccordanceriiththe following
c r i t e r i a on a day with r a i n f a l l and a day without r a i n f a l l .
5 a: V i s i b i l i t y is improved compared t o observation with the naked
eye.
b: There is no change i n v i s i b i l i t y compared t o observation with
the naked eye.
c: Visibilityisdeterioratedcomparedtoobservationwiththenaked
10 eye.
[OllO]
[Refractive Index, Abbe Number]
Measurementriasperformedat20°Cusinga Pulfrichrefractometer
KPR-30 manufactured by Shimadzu Corporation.
15 [Olll]
(Synthesis Example 1)
15.0 g of a compound represented by the following Structural
Formula (2-a) was dissolved i n 150 m l of N,N-dimethylformamide, and
31.8 g of bromine was added dropwise thereto a t 10°C t o 20°C. After
20 s t i r r i n g the mixture for 4 hours a t room temperature, the stirred
mixture was discharged to 700 g of ice water and was neutralized with
asodiumhydroxideaqueous solution. Precipitateswerefilteredout,
washed with water, washed with methanol, and dried t o obtain 31 g
of a compound represented by the following Structural Formula (2-b) .
25 [0112]
[0113]
Next, 26.1 g of the compound represented by Structural Formula
(2-b) , 1.34 g of cuprous iodide, 2.13 g of bis (triphenylphosphine)
5 palladium (11) dichloride, and 1.05 g of triphenylphosphine were
dissolved i n 525 m l of tetrahydrofuran, and 36.4 g of triethylamine
and 21.16 g of 3,3-dimethyl-1-butyne (purity of 96%) were added
thereto. The mixture was s t i r r e d a t room temperature i n a nitrogen
gas stream and the reaction was completed. Then, insoluble matters
10 were f i l t e r e d out, and a f i l t r a t e was concentrated under reduced
pressure. 500 m l of 85% methanol water was added to a concentrated
residue, ,the mixture was s t i r r e d and f i l t e r e d . Then, the f i l t e r e d
mixturewas washedwith 85% methanolwater a n d d r i e d t o o b t a i n a c r u d e
material. The crude material was purified (developing solvent:
15 toluene/hexane=6:4 vol. r a t i o ) using a s i l i c a gel column to obtain
10.8 g of Specific Example Compound (A-1).
[0114]
( A - 1 )
[0115]
MS (m/e) : 1312 (M')
A Shimadzu spectrophotometer UV-1600 manufactured by Shimadzu
5 Corporation was used to measure an absorption spectrum of this
compound at an optical path length of 10 mm of a chloroform solution
thereof at a concentration of 0.01 g/L, and as a result, there was
an absorption peak at 479 nm. In addition, the half-value width of
the peak was 27 nm.
10 [0116]
(Synthesis Example 2)
30.0 g of a compound represented by the following Structural
Formula (3-a) was dispersed in 150 g of 1,1,2-trichloroethane and
60 g of water, and a solution containing 58.7 g of bromine and 60
15 g of 1,1,2-trichloroethane was added dropwise thereto at 50°C to 55OC.
After stirring the reaction solution for 3 hours at 50°C to 55OC, the
reaction solution was cooled to room temperature. A sodium sulfite
aqueous solution (4.2 g of sodium sulfite and 21 g of water) was added
t o the reaction solution and the reaction solution was s t i r r e d for
15 minutes a t room temperature. Next, a sodium hydroxide aqueous
solution (16.2 g of sodium hydroxide and 162 g of water) was added
t o the reaction solution which was then s t i r r e d f o r 30 minutes a t
5 roomtemperature. Precipitateswerefilteredout, washedwithwater,
washed with methanol, and dried t o obtain 45.6 g of a compound
represented by the following Structural Formula (3-b).
[0117]
( 3 - a ) (3-b)
10 [0118]
Next, 40.0 g of the compound represented by Structural Formula
(3-b) , 1.85 g of cuprous iodide, 3.16 g of bis (triphenylphosphine)
palladium (11) dichloride, and 1.55 g of triphenylphosphine were
dissolved in 800 m l of tetrahydrofuran, and 54.91 g of triethylamine
15 and29.2 gof3,3-dimethyl-1-butyne (purityof96%) wereaddedthereto.
The mixture was s t i r r e d a t room temperature in a nitrogen gas stream
and the reaction tias completed. Then, insoluble matters were
f i l t e r e d o u t , anda f i l t r a t e was concentratedunderreducedpressure.
500 m l of methanol was added t o a concentrated residue, the mixture
was stirredand filtered. --Thent,h e filteredrnixturewaswashedwith
methanol and dried to obtain a crude material. The crude material
was purified (developing solvent: toluene/hexane=l:l vol. ratio)
usinga silicagelcolumntoobtain28.6gofSpecificExampleCompound
5 (A-2).
[0119]
10 A Shimadzu spectrophotometer UV-1600 manufactured by Shimadzu
Corporation was used to measure an absorption spectrum of this
compound at an optical path length of 10 mm of a chloroform solution
ataconcentrationofO.Olg/L, andasaresult, therewasanabsorption
peak at 479 nm. In addition, the half-value width of the peak was
15 36 nm.
[0121]
(Example 1)
0.042 g of dibutyltin (11) dichloride, 0.084 g of Zelec UN
manufactured by Stepan Company, 1.05 g of -
2-(2'-hydroxy-5'-t-octylpheny1)-benzotriazole, and 34.4 g of
2,5 (6)- bis (isocyanatomethyl)b icyclo- [2.21 p a n e w ere put into
aflaskwhichhadbeensufficientlydried, toprepareamixedsolution.
5 Next, 0.05 g of the compound (A-l) was dissolved in 100.0 g of
2,5(6)-bis(isocyanatomethyl)bicyclo-[2.2.l]-heptane to prepare a
masterbatch, and 1.0 g of the masterbatch was charged into the
above-describedmixed solution. This mixed solution tias stirred for
1 hour at 25'C and the masterbatch was completely dissolved. Then,
10 16.7 g of pentaerythritol tetrakis(3-mercaptopropionate) and 17.9
gof 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane1iereputinto
this preparation solution. The mixture was stirred for 30 minutes
at 25OC to make a mixed homogeneous solution.
Degassing was performed on this homogeneous solution for 1 hour
15 at 600 Pa and the homogeneous solution was filtered through a 1 pm
PTFE filter. Then, the filtered homogeneous solution was injected
into a 2C plano glass mold with a central'thickness of 2 mm and a
diameter of 80 mm.
[0122]
20 The temperaeure ofthis glass moldwas graduallyincreasedover
16 hours from 25°C to 120°C, and the glass mold was kept warm for 4
hours at 120 OC. The temperature of the glass mold was cooled to room
temperature to obtain a plano lens which was taken out of the glass
mold. The obtained plano lens tias further subjected to annealing
25 for 2 hours at 120°C. The refractive index of the obtained lens xias
1.598 and the Abbe number thereof was 39.3.
T h e e v a l u a t i o n r e s u l t s o f v i s i b i l i t y o f t h e s a m p l e l e n s a r e shown
in Table 1 and the measurement r e s u l t of a transmittance curve is
shown in FIG. 1.
[0123]
(Example 2)
5 0.042 g of d i b u t y l t i n (11) dichloride, 0.084 g of Zelec UN
manufactured by Stepan Company, 1.05 g of
2-(2'-hydroxy-5'-t-octylpheny1)-benzotriaoe, and 34.0 g of
2,s (6) -his (isocyanatomethyl) bicyclo- [2.2.11 -heptane were put i n t o
a f l a s k w h i c h h a d b e e n s u f f i c i e n t l y d r i e d , toprepareamixedsolution.
10 Then, a plano lens was obtained similarly t o Example 1 except t h a t
1 . 4 gofamasterbatchwhichhasbeenproducedthroughthe samemethod
as t h a t i n Example 1 was charged i n t o t h e above-described mixed
solution. The r e f r a c t i v e index of the obtained lens was 1.598 and
the Abbe number thereof was 39.3.
15 Theevaluationresultsofvisibilityofthesamplelensareshown
i n Table 1 and the measurement r e s u l t of a transmittance curve is
shown i n FIG. 1.
[0124]
(Example 3)
20 0.042 g,of d i b u t y l t i n (11) dichloride, 0.084 g of Zelec UN
manufactured by Stepan Company, 1.05 g of
2-(2'-hydroxy-5'-t-octylpheny1)-benzotriazole, and 33.3 g of
2,5 (6) -bis (isocyanatomethyl) bicyclo- 12.2.11 -heptane were put i n t o
aflaskwhichhadbeensufficientlydried,toprepareamixedsolution.
25 Then, a plano lens was obtained similarly t o Example 1 except t h a t
2 . 1 g of amasterbatchwhichhas beenproducedthroughthe samemethod
as t h a t i n harged i n t o t h e above-described mixed
s o l u t i o n . Tile r e f r a c t i v e index of t h e obtained lens was 1.598 and
t h e Abbe number thereof was 39.2.
T h e e v a l u a t i o n r e s u l t s o f v i s i b i l i t y o f t h e s a m p l e l e n s a r e s h o r q n
i n Table 1 and t h e measurement r e s u l t of a t r a n s m i t t a n c e curve is
5 shown i n FIG. 1.
101251
(Example 4 )
0.042 g of d i b u t y l t i n (11) d i c h l o r i d e , 0.084 g of Zelec UN
manufactured by Stepan Company, 1.05 g of
10 2-(2'-hydroxy-5'-t-octylpheny1)-benzotriazole, and 28.4 g of
2,5(6)-bis(isocyanatomethyl)bicyclo-[2.2.1l-heptane were put i n t o
aflaskwhichhadbeensufficientlydried, t o p r e p a r e a m i x e d s o l u t i o n .
Then, a plano lens was obtained s i m i l a r l y t o Example 1 except t h a t
7.0 g o f a m a s t e r b a t c h w h i c h h a s b e e n p r o d u c e d t h r o u g h t h e samemethod
15 as t h a t i n Example 1 w a s charged i n t o the above-described mixed
s o l u t i o n . The r e f r a c t i v e index of t h e obtained l e n s w a s 1.598 and
t h e Abbe number thereof was 39.2.
Theevaluationresultsofvisibilityofthesamplelensareshown
i n Table 1 and the measurement r e s u l t of a t r a n s m i t t a n c e curve is
20 shown i n .FIG. 1.
101261
(Example 5)
0.011 g of d i b u t y l t i n (11) d i c h l o r i d e , 0.070 g of Zelec UN
manufactured by Stepan Company, 1.05 g of
25 2-(2'-hydroxy-5'-t-octylpheny1)-benzotriazole, and 34.3 g of
m-xylylene diisocyanate were put i n t o a f l a s k which had been
s u f f i c i e n t l y dried, t o prepare a mixed s o l u t i o n . Next, 0.05 g of
thecompound (A-1) was dissolvedin100.0 gofm-xylylenediisocyanate
to prepare a masterbatch, and 2.1 g of the masterbatch was charged
into the above-described mixed solution. This mixed solution was
stirredfor1hourat250Candthemasterbatchwascompletelydissolved.
5 Then, 33.6 g of 4-mercaptomethyl-l,8-dimercapto-3,6-dithiaoctane
was put into this preparation solution. The mixture was stirred for
30 minutes at 25OC to make a mixed homogeneous solution.
Degassing was performed on this homogeneous solution for 1 hour
at 600 Pa and the homogeneous solution was filtered through a 1 pm
10 PTFE filter. Then, the filtered homogeneous solution was injected
into a 2C plano glass mold with a central thickness of 2 mm and a
diameter of 80 mm.
[0127]
The temperature ofthis glass moldwas graduallyincreased over
15 16 hours from 25OC to 120°C, and the glass mold was kept warm for 4
hours at 120 OC. The temperature of the glass mold rias cooled to room
temperature to obtain a plano lens which was taken out of the glass
mold. The obtained plano lens rsias further subjected to annealing
for 2 hours at 120°C. The refractive index of the obtained lens was
20 1.665 and the-Abbe number thereof was 31.3.
Themeasurementresultofatransmittance curve is shownin FIG.
2.
[0128]
(Example 6)
25 0.007 g of dibutyltin (11) dichloride, 0.070 g of Zelec UN
manufactured by Stepan Company, 1.05 g of
2-(2'-hydroxy-5'-t-octylpheny1)-benzotriazole, and 33.4 g of
m-xylylene diisocyanate were put into a fTask which had been
sufficiently dried, to prepare a mixed solution. Next, 0.05 g of
thecompound (A-1) wasdissolvedin100.0gofm-xylylenediisocyanate
to prepare a masterbatch, and 2.1 g of the masterbatch was charged
5 into the above-described mixed solution. This mixed solution was
stirredfor1hourat250Candthemasterbatchr~rascompletelydissolved.
Then, 33.6 g of a mixture of
5,7-dimercaptomethyl-l,ll-dimercapto-3,6,9-trithiaundecane,
4,7-dimercaptomethyl-l,11-dimercapto-3,6,9-trithiaundecane, and
10 4,8-dimercaptomethyl-1,ll-dimercapto-3,6,9-trithiaundecane was
put into this preparation solution. The mixture was stirred for 30
minutes at 25OC to make a mixed homogeneous solution.
Degassing was performed on this homogeneous solution for 1 hour
at 600 Pa and the homogeneous solution was filtered through a 1 pm
15 PTFE filter. Then, the filtered homogeneous solution was injected
into a 2C plano glass mold with a central thickness of 2 mm and a
diameter of 80 mm.
The temperature of this glass mold was gradually increased over
20 16 hours from'25OC to 120°C, and the glass mold was kept warm for 4
hours at 120 OC. The temperature of the glass mold was cooled to room
temperature to obtain a plano lens which was taken out of the glass
mold. The obtained plano lens was further subjected to annealing
for 2 hours at 120°C. The refractive index of the obtained lens was
25 1.668 and the Abbe number thereof was 31.1.
The measurement result of a transmittance curve is shown in FIG.
.--[0130] . -.
(Example 7)
0.006 g of dibutyltin (11) dichloride, 0.070 g of Zelec UN
manufactured by Stepan Company, 1.05 g of
5 2-(2'-hydroxy-5'-t-octylpheny1)-benzotriazole, and 28.4 g of
m-xylylene diisocyanate were put into a flask which had been
sufficiently dried, to prepare a mixed solution. Next, 0.05 g of
thecompound (A-1) wasdissolvedin100.0gofm-xylylenediisocyanate
to prepare a masterbatch, and 2.1 g of the masterbatch was charged
10 into the above-described mixed solution. This mixed solution was
stirred for 1 hour at 25°C and the masterbatch was completely dissolved.
Then, 39.5 g of pentaerythritoltetrakis(3-mercaptopropionate) was
put into this preparation solution. The mixture was stirred for 30
minutes at 25OC to make a mixed homogeneous solution.
15 Degassing was performed on this homogeneous solution for 1 hour
at 600 Pa and the homogeneous solution was filtered through a 1 pm
PTFE filter. Then, the filtered homogeneous solution was injected
into a 2C plano glass mold with a central thickness of 2 mm and a
diameter of 80 mm.
20 [0131]
The temperature ofthis glass mold was graduallyincreased over
16 hours from 25OC to 12OoC, and the glass mold was kept warm for 4
hours at 120 "C. The temperature of the glass mold was cooled to room
temperature to obtain a plano lens which was taken out of the glass
25 mold. The obtained plano lens was further subjected to annealing
for 2 hours at 120°C. The refractive index of the obtained lens was
1.598 and the Abbe number thereof rsias 36.4.
.. Themeasurement result of atransmittance curve is shownin FIG.
2.
[0132]
(Example 8)
5 0.035 g of dimethyltin (11) dichloride, 0.070 g of Zelec UN
manufactured by Stepan Company, 1.05 g of
2-(2'-hydroxy-5'-t-octylpheny1)-benzotriaole and 35.9 g of
2,s (6)- bis (isocyanatomethyl)b icyclo- 12.2 1 e t awe re put into
a flaskwhichhadbeensufficientlydried,toprepareamixedsolution.
10 Next, 0.05 g of the compound (A-1) was dissolved in 100.0 g of
2,5(6)-bis(isocyanatomethyl)bicyclo-~2.2.ll-heptane to prepare a
masterbatch, and 2.1 g of the masterbatch was charged into the
above-describedmixedsolution. Thismixedsolution was stirred for
1 hour at 25OC and the masterbatch was completely dissolved. Then,
15 32.0 g of 4-mercaptornethyl-l,8-dimercapto-3,6-dithiaoctane was put
into this preparation solution. The mixture was stirred for 30
minutes at 2S°C to make a mixed homogeneous solution.
Degassing was performed on this homogeneous solution for 1 hour
at 600 Pa and the homogeneous solution was filtered through a 1 pm
20 PTFE filter. Then, the filtered homogeneous solution was injected
into a 2C plano glass mold with a central thickness of 2 mm and a
diameter of 80 mm.
The temperature of this glass mold rias gradually increased over
25 16 hours from 25OC to 120°C, and the glass mold was kept warm for 4
hours at 120 OC. The temperature of the glass mold was cooled to room
o lens which was taken out of the glass
mold. The obtained plano lens was further subjected to annealing
for 2 hours at 120°C. The refractive index of the obtained lens was
1.616 and the Abbe number thereof tias 37.9.
Themeasurementresultofatransmittance curve is shown in FIG.
5 3.
[a1341
(Example 9)
0.035 g of dibutyltin (11) dichloride, 0.070 g of Zelec UN
manufactured by Stepan Company, 1.05 g of
10 2-(2'-hydroxy-5'-t-octylpheny1)-benzotriazole, and 32.7 g of
2,5 (6)- bis (isocyanatomethyl)b icyclo- c2.2.11 -heptane were put into
a flaskwhichhadbeensufficientlydried, toprepareamixedsolution.
Next, 0.05 g of the compound (A-1) was dissolved in 100.0 g of
2,5 (6) -bis (isocyanatomethyl) bicyclo- [2.2.1] -heptane to prepare a
15 masterbatch, and 2.1 g of the masterbatch %.>as charged into the
above-describedmixed solution. Thismixedsolutionrvas stirred for
1 hour at 25'C and the masterbatch was completely dissolved. Then,
17.1 g of pentaerythritol tetrakis(3-mercaptopropionate) and 18.1
g of a mixture of
4,7-dimercaptomethyl-l,ll-dimercapto-3,6,9-trithiaundecane, and
4,8-dimercaptomethyl-l,ll-dimercapto-3,6,9-trithiaundecane were
put into this preparation solution. The mixture was stirred for 30
minutes at 25OC to make a mixed homogeneous solution.
25 Degassing was performed on this homogeneous solution for 1 hour
at 600 Pa and the homogeneous solution was filtered through a 1 pm
PTFE filter. Then, the filtered homogeneous solution was injected
i n t o a 2C plano glass mold with a c e n t r a l thickness of 2 mm a n d ~ a
diameter of 80 mm.
LO1351
The temperature o f t h i s glassmold was graduallyincreasedover
5 16 hours from 25'C t o 120°C, and the glass mold was kept warm for 4
hours a t 120 'C. The temperature of the glass mold was cooled to room
temperature to obtain a plano lens which was taken out of the glass
mold. The obtained plano lens was f u r t h e r subjected t o annealing
for 2 hours a t 120°C. The refractive index of the obtained lens was
10 1.597 and the Abbe number thereof was 39.2.
Themeasurement r e s u l t of atransmittance curve is shown i n FIG.
3.
[0136]
(Example 10)
15 0.035 g of dimethyltin (11) dichloride, 0.070 g of Zelec UN
manufactured by Stepan Company, 1.05 g of
2-(2'-hydroxy-5'-t-octylpheny1)-benzotriaole and 35.0 g of
2,5 (6) -bis (isocyanatomethyl) bicyclo- r2.2.11 -heptane were put i n t o
aflaskwhichhadbeensufficientlydried, toprepareamixedsolution.
20 Next, 0.05 g of the compound (A-1) was dissolved i n 100.0 g of
2,5 (6) -bis (isocyanatomethyl) bicyclo- 12.2 1 -heptane t o prepare a
masterbatch, and 2.1 g of the masterbatch was charged into the
above-describedmixed solution. Thismixed solutionwas s t i r r e d f o r
1 hour a t 25°C and the masterbatch was completely dissolved. Then,
25 32.9 g of a mixture of
4,7-dimercaptomethyl-l,ll-dimercapto-3,6,9-trithiaundecane, and
4,8-dimercaptomethyl-l,ll-dimercapto-3,6,9-trithiaundecane was
put into this preparation solution. The mixture was stirred for 30
minutes at 25'C to make a mixed homogeneous solution.
Degassing was performed on this homogeneous solution for 1 hour
5 at 600 Pa and the homogeneous solution was filtered through a 1 pm
PTFE filter. Then, the filtered homogeneous solution was injected
into a 2C plano glass mold with a central thickness of 2 rnrn and a
diameter of 80 mrn.
[0137]
10 The temperature ofthis glassmoldwas graduallyincreasedover
16 hours from 25OC to 120°C, and the glass mold was kept warm for 4
hours at 120 O C . The temperature of the glass mold was cooled to room
temperature to obtain a plano lens which was taken out of the glass
mold. The obtained plano lens was further subjected to annealing
15 for 2 hours at 120°C. The refractive index of the obtained lens was
1.618 and the Abbe number thereof was 38.6.
Themeasurement result of atransmittance curve is shownin FIG.
3.
[0138]
20 (Example 11)
0.035 g of dimethyltin (11) dichloride, 0.070 g of Zelec UN
manufactured by Stepan Company, 1.05 g of
2-(2'-hydroxy-5'-t-octylpheny1)-benzotriazole, and 30.0 g of
2,5 (6)- his (isocyanatomethyl)b icyclo- C2.2.11 -heptane were put into
25 aflaskwhichhadbeensufficientlydried,toprepareamixedsolution.
Next, 0.05 g of the compound (A-1) was dissolved in 100.0 g of
2,5(6)-bis(isocyanatomethyl)bicyclo-[2.2.1]-heptane to prepare a
masterbatch, and 2.1 g of the masterbatch was charged into the
above-describedmixedsolution. Thismixed solutionwas stirred for
1 hour at 25OC and the masterbatch was completely dissolved. Then,
37.9 g of pentaerythritol tetrakis(3-mercaptopropionate) was put
5 into this preparation solution. The mixture was stirred for 30
minutes at 25OC to make a mixed homogeneous solution.
Degassing was performed on this homogeneous solution for 1 hour
at 600 Pa and the homogeneous solution was filtered through a 1 pm
PTFE filter. Then, the filtered homogeneous solution was injected
10 into a 2C plano glass mold with a central thickness of 2 mm and a
diameter of 80 mm.
[0139]
The temperature ofthis glass moldwas graduallyincreased over
16 hours from 25OC to 120°C, and the glass mold was kept warm for 4
15 hours at 120 OC. The temperature of the glass mold was cooled to room
temperature to obtain a plano lens which was taken out of the glass
mold. The obtained plano lens was further subjected to annealing
for 2 hours at 120°C. The refractive index of the obtained lens was
1.568 and the Abbe number thereof was 41.2.
20 The measucrernent result of a transmittance curve is shotbm in FIG.
3.
[0140]
(Example 12)
A plano lens was obtained through the same method as that in
25 Example 3 except that the compound (A-1) was changed to the compound
(A-2). The obtained plano lens was further subjected to annealing
for 2 hours at 120°C. The refractive index of the obtained lens was
1.598 and the- Abbe number thereof was 39.2.
Themeasurement result of atransmittance curve is shownin FIG.
3.
[0141]
5 (Comparative Example 1)
A plano lens was obtained through the same method as that in
Example 1 except that the amount of
2,5(6)-bis(isocyanatomethyl)bicyclo-[2.2.l]-heptane which was put
was set to 35.4 g and the masterbatch of the compound (A-1) was not
10 used. The obtained plano lens was further subjected to annealing
for 2 hours at 120°C.
TheevaluationresultsofvisibilityoEthesamplelensareshown
in Table 1.
[0142]
15 (Comparative Example 2)
0.035 g of dimethyltin (11) dichloride, 0.070 g of Zelec UN
manufactured by Stepan Company, 1.05 g of
2-(2'-hydroxy-5'-t-octylpheny1)-benzotriaole 0.0175 g of the
compound A - , and 35.4 g of
20 2,s (6)- bis (i6ooyanatomethyl)b icyclo- 12.2.11 -heptane were put into
aflaskwhichhadbeensufficientlydried,toprepareamixedsolution.
This mixed solution was stirred for 1 hour at 25OC and the masterbatch
was completely dissolved. Then, 16.7 g of pentaerythritol
tetrakis(3-mercaptopropionate) and 17.9 g of
25 4-mercaptomethyl-l,8-dimercapto-3,6-dithiaoctane were put into
this preparation solution. The mixture was stirred for 30 minutes
at 25OC to make a mixed homogeneous solution.
Degassing was performed on this homogeneous solution for 1 hour
at 600 Pa and the homogeneous solution was filtered through a 1 pm
PTFE filter. Then, the filtered homogeneous solution was injected
into a 2C plano glass mold with a central thickness of 2 rnm and a
5 diameter of 80 mm.
[01431
The temperature ofthis glassmoldwas graduallyincreased over
16 hours from 25OC to 120°C, and the glass mold was kept warm for 4
hours at 120 "C. The temperature of the glass mold rvas cooled to room
10 temperature to obtain a plano lens which was taken out of the glass
mold. The obtained plano lens was further subjected to annealing
for 2 hours at 120°C. The refractive index of the obtained lens was
1.598 and the Abbe number thereof was 38.5.
The measurement result of a transmittance curve is shown in FIG.
15 4.
[01441
(Comparative Example 3)
A plano lens was obtained through the same method as that in
Comparative Example 2 except that 0.0175 g of the compound (A-1) was
20 changed to 0.035 g. The obtained plano lens was further subjected
to annealing for 2 hours at 120°C. The refractive index of the
obtained lens was 1.598 and the Abbe number thereof was 38.1.
Themeasurement result of atransmittance curve is shownin FIG.
4.
Table -1
b: There is no change i n v i s i b i l i t y compared t o observation with
Example 4
the naked eye.
c: Visibilityisdeterioratedcomparedtoobservationwiththenaked
without
-r-a i-n f a l l
with
r a i n f a l l
eye.
[0146]
b
--
C
P r i o r i t y is claimed on Japanese Patent Application No.
2013-187735, filedSepternber10, 2013, t h e e n t i r e d i s c l o s u r e o f which
b
a
is incorporated herein by reference
a: Visibilityisimprovedcomparedto observationwith the nakedeye.
b
C
The present invention includes the following modes.
a
a
[ I ] An o p t i c a l material i n which a transmittance curve measured a t
b -
C
a thickness of 2 mm of t h e o p t i c a l material s a t i s f i e s the following
a
a
c h a r a c t e r i s t i c s (1) to ( 4 ) ,
(1) the transmittance curve has a maximum transmittance value
b
C
inawavelengthrangeof 400nmto 440 nmandthemaximumtransmittance
c
C
a
a
a
a
thereof is 50% or more,
(2) the transmittance curve has a minimum transmittance value
in a wavelength range of 471 nm to 500 nm,
(3) the transmittance at a wavelength of 540 nm is 60% or more,
5 and
(4) the minimum transmittance value in the wavelength range of
471 nm to 500 nm is seven-tenths or less of the maximum transmittance
in the i.lavelength range of 400 nm to 440 nm and is seven-tenths or
less of the transmittance at 540 nm.
10 [2] The optical material according to [I], including:
at least one kind of organic dyes inn which an absorption peak
is in a wavelength range of 471 nm to 490 nm and the half-value width
of the absorption peak is 10 nm or more and less than 50 nm, in an
absorption spectrum which is measured at an optical path length of
15 10 mm of a chloroform solution thereof at a concentration of 0.01
g/L.
[3] The optical material according to [2],
in which the organic dyes are one or more compounds selected
fromporphyrin-based compounds represented by the followingGenera1
20 Formula (A) -
R3
I n t h e formula, XltoXseachindependentlyrepresentahydrogen
atom; a straightorbranchedalkylgroup; anethynylgroup; anethynyl
group substituted with t h e s t r a i g h t or branched alkyl group; an
5 ethynyl group having a phenyl group; or an ethynyl group having a
phenyl group substituted with the s t r a i g h t or branched alkyl group.
A l l of X1 t o Xg are not hydrogen atoms a t same time. R1 t o Rg each
independently represent a hydrogen atom; and a s t r a i g h t or branched
alkylgroup. Mrepresentstwohydrogenatoms, adivalentmetalatom,
10 a t r i v a l e n t .substituted metal atom, a t e t r a v a l e n t s u b s t i t u t e d metal
atom, a hydroxylated metal atom, or an oxidized metal atom.
[ 4 ] Theopticalmaterial accordingto 121 or [ 3 ] , including: a t l e a s t
one kind selected frompolyurethane, polythiourethane, polysulfide,
polycarbonate, poly(meth)acrylate, and polyolefin.
15 151 A composition for an o p t i c a l material, including:
a resin f o r an o p t i c a l material or a resin monomer; and
a t l e a s t one kind of organic dyes i n which an absorption peak
. . is i n a wavelength range of 471 nrn to 490 nm and the half-value width
of the absorption peak is 10 nm or more and l e s s than 50 nm, i n an
absorption spectrum which is measured a t an o p t i c a l path length of
10 mm of a chloroform solution thereof a t a concentration of 0.01
5 g/L.
[6] The composition for an o p t i c a l material according t o 151,
i n which the organic dyes are one or more compounds selected
fromporphyrin-based compounds represented by the following General
Formula ( A ) .
In the formula, XltoXseachindependently representahydrogen
atom; a straightorbranchedalkylgroup; anethynylgroup; anethynyl
group substituted with the s t r a i g h t or branched alkyl group; an
ethynyl group having a phenyl group; or an ethynyl group having a
15 phenylgroup substituted with the s t r a i g h t or branched alkyl group.
A l l of XI t o X8 are not hydrogen atoms a t same time. R1 t o Rq each
independently represent a hydrogen atom; and a s t r a i g h t or branched
alkylgroup. Mrepresentstwohydrogen atoms, a divalent metal atom,
a trivalent substituted metal atom, a tetravalent substituted metal
atom, a hydroxylated metal atom, or an oxidized metal atom.
171 The composition for an optical material according to 161,
5 in which the resin for an optical material is at least one kind
selected from polyurethane, polythiourethane, polysulfide,
polycarbonate, poly(meth)acrylate, and polyolefin.
[81 A process for producing a molded product, including:
a step of obtaining the composition for an optical material
10 according to any one of [51 to 171 by mixing the organic dyes with
the resin for an optical material or the resin monomer; and
a step of curing the composition for an optical material.
[9] A molded product which is obtained by molding the composition
for an optical material according to any one of [5] to [ 7 ] .
15 [lo] An optical material comprised of the molded product according
to 191.
I111 A plastic spectacle lens comprised of the optical material
according to any one of [I] to [4] and [lo].
[I23 A plastic spectacle lens,
20 inrvhichalensbasematerialiscomprisedoftheopticalmaterial
according to any one of [I] to [4] and [lo].
1131 A film comprised of the molded product according to [9].
1141 A plastic spectacle lens, including:
a film layer over at least one surface of a lens base material,
25 in which the film layer is comprised of the film according to
[131.
1151 A plastic spectacle lens including:
a coating l a y e r o v e r a t l e a s t one surface o f a l e n s basematerial,
in which the coating layer is comprised of the composition for
an o p t i c a l material according t o any one of [ 5 ] to [ 7 ] .
CLAIMS
1. An optical material in which a transmittance curve measured a t
a thickness of 2 mmthereof s a t i s f i e s the following c h a r a c t e r i s t i c s
5 (1) t o ( 4 ) ,
(1) the transmittance curve has a maximum transmittance value
inawavelengthrangeof 400nmto 440 nmandthemaximumtransmittance
thereof is 50% or more,
(2) the transmittance curve has a minimum transmittance value
10 i n a wavelength range of 471 nm t o 500 nm,
(3) the transmittance a t a wavelength of 540 nm is 60% or more,
and
( 4 ) the minimum transmittance value i n the wavelength range of
471 nm t o 500 nm is seven-tenths or less of the maximum transmittance
15 i n the wavelength range of 400 nm t o 440 nm and is seven-tenths or
less of the transmittance a t 540 nm.
2. The o p t i c a l material according t o claim 1,
wherein theminimumtransmittance value in the wavelength range
20 of 471 nm to.500 nm is 60% or l e s s .
3. The o p t i c a l material according to claim 1 or 2, comprising:
a t l e a s t one kind of organic dyes i n which an absorption peak
is in a wavelength range of 471 nm t o 490 nm and the half-value width
25 of the absorption peak is 10 nm or more and l e s s than 50 nm, in an
absorption spectrum which is measured a t an o p t i c a l path length of
10 mm of a chloroform solution thereof a t a concentration of 0.01
4 . The o p t i c a l material according t o claim 3,
wherein the amount of the organic dyes is 5 ppm to 100 ppm.
5
5. The o p t i c a l material according t o claim 3 or 4,
r*rhereintheorganicdyes are one ormore compounds selected from
porphyrin-based compounds represented by the folloriing General
Formula (A) :
RI
wherein XI t o X8 each independently represent a hydrogen atom,
a straightorbranchedalkylgroup, anethynylgroup, anethynyl group
substituted with t h e s t r a i g h t or branched alkyl group, an ethynyl
grouphavingaphenylgroup, or an ethynyl group havingaphenylgroup
15 substituted with t h e s t r a i g h t or branched alkyl group; a l l of XI t o
X8 are not hydrogen atoms a t same t i m e ; R1 t o R4 each independently
represent a hydrogen atom, and a s t r a i g h t or branched alkyl group;
andMrepresentstwohydrogenatoms, adivalentmetalatom, atrivalent
substituted metal atom, a tetravalent substituted metal atom, a
hydroxylated metal atom, or an oxidized metal atom.
5 6. The optical material according to any one of claims 3 to 5,
comprising: at least one kind selected from polyurethane,
polythiourethane, polysulfide, polycarbonate, poly(meth)acrylate,
and polyolefin.
10 7. The optical material according to any one of claims 3 to 6,
comprising: polythiourethane.
8. The optical material according to claim 6 or 7,
. . . ., .~,. .
whereinthepolythiourethaneis comprisedof a constituent unit
15 derived fromapolyisocyanate compoundanda constituent unitderived
from a polythiol compound,
wherein the polyisocyanate compound is at least one kind
selected from 2,5-bis(isocyanatomethyl)bicyclo-[2.2.1]-heptaner
2,6-bis(isocyanatomethyl)bicyclo-[2.2.1l-heptane, m-xylylene
20 diisocyanate, dicyclohexylmethane diisocyanate,
bis(isocyanatomethyl)cyclohexane, isophorone diisocyanate,
1,6-hexamethylene diisocyanate, and 1,5-pentamethylene
diisocyanate, and
wherein the polythiol compound is at least one kind selected
25 from 4-mercaptomethyl-l,8-dimercapto-3,6-dithiaoctane,
4,8-dimercaptomethyl-l,ll-dimercapto-3,6,9-trithiaundecane,
pentaerythritol tetrakis(3-mercaptopropionate),
bis(mercaptoethyl)sulfide, pentaerythritol
tetrakis(2-mercaptoacetate), 2,5-bis(mercaptomethy1)-1,4-dithiane,
5 1,1,3,3-tetrakis (mercaptomethylthio)propane,
4,6-bis (mercaptomethylthio)- 1,3-dithiane, and
2- (2,2-bis( mercaptomethylthio)e thyl)- l,3-dithietane.
9. A composition for an optical material, comprising:
10 a resin for an optical material or a resin monomer; and
at least one kind of organic dyes in which an absorption peak
is in a wavelength range of 471 nm to 490 nm and the half-value width
of the absorption peak is 10 nm or more and less than 50 nm, in an
absorption spectrum rsrhich is measured at an optical path length of
15 10 mm of a chloroform solution thereof at a concentration of 0.01
g/L,
wherein the amount of the organic pigment is 0.0005 parts by
weight to 0.01 parts by weight with respect to 100 parts by weight
in total of the resin for an optical material or the resin monomer.
20 , , ,
10. The composition for an optical material according to claim 9,
wherein the organicdyes are one ormore compounds selected from
porphyrin-based compounds represented by the following General
Formula (A) :
wherein X1 t o X8 each independently represent a hydrogen atom,
a straightorbranchedalkylgroup, anethynylgroup, anethynylgroup
substituted with t h e s t r a i g h t or branched alkyl group, an ethynyl
5 grouphavingaphenylgroup, oranethynylgrouphavingaphenylgroup
s u b s t i t u t e d with the s t r a i g h t or branched alkyl group; a l l of X1 t o
Xg are not hydrogen atoms a t same time; R1 t o Rq each independently
represent a hydrogen atom, and a s t r a i g h t or branched alkyl group;
andMrepresentstwohydrogenatoms, adivalentmetalatom, a t r i v a l e n t
10 substituted[metal atom, a t e t r a v a l e n t s u b s t i t u t e d metal atom, a
hydroxylated metal atom, or an oxidized metal atom.
11. The composition for an o p t i c a l material according t o claim 9
15 wherein the resin for an o p t i c a l material is a t l e a s t one kind
selected from polyurethane, polythiourethane, polysulfide,
polycarbonate, poly(rneth)acrylate, and polyolefin.
12. The composition for an optical material according to any one
of claims 9 to 11,
wherein the resin for an optical-material is polythiourethane.
13. The composition for an optical material according to any one
of claims 9 to 12,
wherein the resin monomer is a polyisocyanate compound and a
polythiol compound.
10
1 4 . The composition for an optical material according to claim 13,
wherein the polyisocyanate compound is at least one kind
selected from 2,5-bis(isocyanatomethyl)bicyclo-[2.2.1]-heptane,
2,6-bis (isocyanatomethyl)b icyclo- r2.2.11 -hptane, m-xylylene
15 diisocyanate, dicyclohexylmethane diisocyanate,
1,3-bis (isocyanatomethyl) cyclohexane,
1,4-bis(isocyanatomethyl)cyclohexane, isophorone diisocyanate,
1,6-hexamethylene diisocyanate, and 1,5-pentamethylene
diisocyanate, and
20 wherein the polythiol compound is at least one kind selected
from 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane,
25 pentaerythritol tetrakis(3-mercaptopropionate),
bis(mercaptoethyl)sulfide, pentaerythritol
tetrakis (2-mercaptoacetate), 2,5-b methyl) -l,4-dithia
1,1,3,3-tetrakis(mercaptornethylthio)propane,
4,6-bis (mercaptomethylthio)- 1,3-dithiane, and
2-(2,2-bis(rnercaptomethylthio)ethyl)-1,3-dithietane.
5 15. A process for producing a molded product, comprising:
a step of obtaining the composition for an optical material
according to any one of claims 9 to 14 by mixing the organic dyes
with the resin for an optical material or the resin monomer; and
a step of curing the composition for an optical material.
10
16. The process for producing a molded product according to claim
15,
wherein the resin monomer is a polyisocyanate compound and a
polythiol compound.
15
17. The process for producing a molded product according to claim
15 or 16,
wherein the resin monomer is the polyisocyanate compound and
the polythiol compound,
20 wherein the polyisocyanate compound is at least one kind
selected from 2,5-bis (isocyanatomethyl) bicyclo- [2.2.1] -heptane,
2,6-bis(isocyanatomethyl)bicyclo-[2.2.1]-heptane, m-xylylene
diisocyanate, dicyclohexylmethane diisocyanate,
1,3-bis (isocyanatomethyl) cyclohexane,
25 1,4-bis(isocyanatomethyl)cyclohexane, isophorone diisocyanate,
1,6-hexamethylene diisocyanate, and 1,5-pentamethylene
diisocyanate, and
wherein the polythiol compound is at least one kind selected
from 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane,
5,7-dimercaptomethyl-l,ll-dimercapto-3,6,9-trithiaundecane,
4,7-dimercaptomethyl-l,ll-dimercapto-3,6,9-trithiaundecane,
5 4,8-dimercaptomethyl-l,ll-dimercapto-3,6,9-trithiaundecane,
pentaerythritol tetrakis(3-mercaptopropionate),
bis(mercaptoethyl)suIfide, pentaerythritol
tetrakis(2-mercaptoacetate), 2,5-bis(mercaptomethy1)-1,4-dithiane,
1,1,3,3-tetrakis (mercaptomethylthio)propane,
10 4,6-bis (mercaptomethylthio) -l,3-dithiane, and
2- (2,2-bis( mercaptomethylthio)e thyl)- 1,3-dithietane.
18. A molded product which is obtained by polymerizing and curing
the composition foranopticalmaterial accordingtoanyoneof claims
15 9 to 14.
19. An optical material comprised of the molded product according
to claim 19.
20 20. A plastiic~spectacle lens comprised of the optical material
according to any one of claims 1 to 8 and 19.
21. A plastic spectacle lens,
whereinalensbasematerialiscomprisedoftheopticalmaterial
25 according to any one of claims 1 to 8 and 19.
22. A film comprised of the molded product according to claim 18.
23. A plastic spectacle lens, comprising:
a film layer over at least one surface of a lens base material,
wherein the film layer is comprised of the film according to
5 claim 22.
24. A plastic spectacle lens comprising:
a coating layer over at least one surface of a lens basematerial,
wherein the coating layer is comprised of the composition for
10 an optical material according to any one of claims 9 to 14.