CN100384895C - Actinic-energy-ray-curable composition for optical material - Google Patents
Actinic-energy-ray-curable composition for optical material Download PDFInfo
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- CN100384895C CN100384895C CNB2004800325510A CN200480032551A CN100384895C CN 100384895 C CN100384895 C CN 100384895C CN B2004800325510 A CNB2004800325510 A CN B2004800325510A CN 200480032551 A CN200480032551 A CN 200480032551A CN 100384895 C CN100384895 C CN 100384895C
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Abstract
This invention provides an actinic-energy-ray-curable composition for optical materials which can give a cured article having a high refractive index, high light transmittance, and low water absorption. The actinic-energy-ray-curable composition for optical materials comprises (A) a di(meth)acrylate represented by the formula(1) and (B) a mono(meth)acrylate represented by the formula (2) and/or mono(meth)acrylate represented by the formula (3). Also provided is a process for producing an optical material which comprises applying or pouring the composition to a casting mold and then irradiating it with actinic energy rays. In formula(1): R1 and R3 each independently represents hydrogen or methyl; R2 and R4 each independently represents hydrogen, methyl, or ethyl; R5 to R8 each independently represents hydrogen, methyl, or bromine; and l and m each independently is an integer of 1 to 6. In formula(2): R9 represents hydrogen or methyl, R10 represents hydrogen or methyl.
Description
Technical field
The present invention relates to actinic-energy-ray-curable composition for optical material, belong to the technical field of optical materials such as active energy ray-curable composition and lens and plastic lens.
Background technology
In the past, lens such as Fresnel lens and biconvex lens formed by methods such as compression molding and castings and made.
But, in the former compression molding, make owing to circulating according to heating, pressurization and refrigerative, there is the problem of productivity difference.In addition, in the latter's the casting, carry out polymerization in order to inject monomer in mould, the Production Time of cost is longer, needs a plurality of moulds simultaneously, so there is the high problem of manufacturing cost.
On the other hand, because the active energy ray-curable composition has the voltinism of tachy steroling, and highly productive, in order to address the above problem, the manufacturing active energy ray-curable composition at lens has proposed various schemes (for example patent documentation 1～6).
But, active energy ray-curable composition in the past specific refractory power and transparent aspect exist not enough, in order to improve this point, studied by bisphenol type two (methyl) acrylate and list (methyl) acrylate and also used the composition (for example, patent documentation 7 and patent documentation 8) that obtains with aromatic ring.
Patent documentation 1: the spy opens clear 61-177215 communique (claim)
Patent documentation 2: the spy opens clear 61-248707 communique (claim)
Patent documentation 3: the spy opens clear 61-248708 communique (claim)
Patent documentation 4: the spy opens clear 63-163330 communique (claim)
Patent documentation 5: the spy opens clear 63-167301 communique (claim)
Patent documentation 6: the spy opens clear 63-199302 communique (claim)
Patent documentation 7: the spy opens flat 9-87336 communique (claim)
Patent documentation 8: patent 3397448 communiques (claim)
Summary of the invention
But in the active energy ray-curable composition that uses in optical applications, above-mentioned composition is desired in the slimming as projection TV etc., require to have exist aspect the purposes of more high refractive index and the transparency not enough.
In addition, for the active energy ray-curable composition that in optical applications, uses,, also require the dimensional stability of the cured article make except these optical characteristics.That is, when the water-intake rate of cured article was high, suction caused dimensional change when long, produced inhomogeneously sometimes aspect optical characteristics, caused peeling off, being out of shape of member sometimes.
In order to find that in the cured article that makes specific refractory power is high and have the high light line transmissivity, and water-intake rate is little, the actinic-energy-ray-curable composition for optical material of excellent size stability, and the present inventor has carried out wholwe-hearted research.
The present inventor has carried out various researchs in order to address the above problem, found that the quick solidifying that the composition that contains specific two kinds of (methyl) acrylate is caused by active energy ray, and the specific refractory power height of its cured article, light transmittance is good, thereby has finished the present invention.
Below, the present invention is described in detail.
In this manual, acrylate or methacrylic ester are represented with (methyl) acrylate.
The present invention relates to a kind of actinic-energy-ray-curable composition for optical material, described composition is by forming with two (methyl) acrylate (A) of aftermentioned general formula (1) expression and list (methyl) acrylate (B) represented with list (methyl) acrylate of aftermentioned general formula (2) expression or/and with aftermentioned general formula (3); With (A) composition and (B) total amount of composition contain (A) composition 10～90 quality % and (B) composition 90～10 quality % in the described composition as benchmark.
Below, each composition is described.
1. (A) composition
(A) composition is following two (methyl) acrylate with general formula (1) expression.
[in the formula (1), R
1And R
3Represent hydrogen atom or methyl, R respectively independently
2And R
4Represent hydrogen atom, methyl or ethyl, R respectively independently
5～R
8Represent hydrogen atom, methyl or bromine atoms respectively independently, l and m represent 1～6 integer respectively independently.]
As R
1And R
3,, preferably all be hydrogen atom for the solidified nature that makes composition is good.As R
2And R
4,, preferably all be hydrogen atom for the specific refractory power that makes resulting cured article is good.As R
5～R
8, the yield height when making manufacturing (A) composition, and the specific refractory power of resultant cured article is good, preferred R
5～R
8It all is hydrogen atom; Or R
5Be hydrogen atom, R
6Be methyl, and R
7Be hydrogen atom, R
8It is methyl; And R
5Be hydrogen atom, R
6Be bromine atoms, and R
7Be hydrogen atom, R
8It is bromine atoms.
As l and m,, be preferably 1～3 for the specific refractory power that makes the cured article that makes is good.
As the object lesson of (A) composition, can list two (4-methacryloxy ethoxyl phenenyl) sulfide, two (4-acryloxy ethoxyl phenenyl) sulfide, two (4-methacryloxy diethoxy phenyl) sulfide, two (4-acryloxy diethoxy phenyl) sulfide, two (4-methacryloxy triethoxy phenyl) sulfide, two (4-acryloxy triethoxy phenyl) sulfide, two (4-methacryloxy diethoxy-3-aminomethyl phenyl) sulfide, two (4-acryloxy diethoxy-3-aminomethyl phenyl) sulfide, two (4-methacryloxy oxyethyl group-3-bromophenyl) sulfide, two (4-acryloyl-oxy base oxethyl-3-bromophenyl) sulfide, two (4-methacryloxy diethoxy-3-bromophenyl) sulfide and two (4-acryloxy diethoxy-3-bromophenyl) sulfide etc.
Wherein, from the good viewpoint of solidified nature, more preferably two (4-acryloxy ethoxyl phenenyl) sulfide, two (4-acryloxy diethoxy phenyl) sulfide, two (4-acryloyl-oxy base oxethyl-3-aminomethyl phenyl) sulfide and two (4-acryloxy diethoxy-3-aminomethyl phenyl) sulfide.
(A) composition can be used in combination a kind of, two kinds or more kinds of.
2. (B) composition
(B) list (methyl) acrylate (hereinafter referred to as (B-2) composition) represented with following general formula (2) expression (methyl) acrylate (hereinafter referred to as (B-1) composition) or/and with following general formula (3) of composition, be give the cured article of composition with high refractive index and low water absorption, make composition become the composition of easy-to-handle liquid state.
(in the formula (2), R
9Expression hydrogen atom or methyl.)
(in the formula (3), R
10Expression hydrogen atom or methyl.)
As the object lesson of (B-1) composition, can list (methyl) vinylformic acid-o-phenyl phenyl ester, (methyl) vinylformic acid-m-phenyl phenyl ester and (methyl) vinylformic acid-p-phenyl phenyl ester.
Wherein, under the room temperature liquid state and easy handling, the viewpoint that is easy to make, preferred (methyl) vinylformic acid-o-phenyl phenyl ester.
Different with (B-1) of the present invention composition and have (methyl) acrylate of a phenyl or have the compound of epoxy alkyl, can not make the cured article of composition have high refractive index, and make cured article water-intake rate height.
As the object lesson of (B-2) composition, can list p-cumyl phenol (methyl) acrylate etc.
Different with (B-2) of the present invention composition and have (methyl) acrylate of a phenyl, can not make the cured article of composition have high refractive index.
(B-1) composition and (B-2) composition can be used in combination a kind of, two kinds or more kinds of.
As (B-1) composition and (B-2) composition and the ratio of time spent, preferred (B-1) composition be 10～90 quality % and (B-2) composition be 90～10 quality %.
3. other composition
Composition of the present invention is cured by the irradiation active energy ray, and the active energy ray as this moment can list electron rays, visible light and ultraviolet ray etc.Wherein, preferred visible light or ultraviolet ray, because it does not need special device, and simple.
Under the situation that forms visible light or ultraviolet-curable composition, mixed light polymerization starter in composition.In addition, under the situation that forms electron(beam)curing type composition, not necessarily need the mixed light polymerization starter.
Object lesson as Photoepolymerizationinitiater initiater (hereinafter referred to as (C) composition) can list bitter almond oil camphor classes such as bitter almond oil camphor, benzoin methylether and bitter almond oil camphor propyl ether; Methyl phenyl ketone, 2,2-dimethoxy-2-phenyl methyl phenyl ketone, 2,2-diethoxy-2-phenyl methyl phenyl ketone, 1,1-dichloroacetophenone, 1-hydroxycyclohexylphenylketone, 2-methyl isophthalic acid-(4-(methylthio group) phenyl)-2-morpholino-propane-1-ketone and N, acetophenones such as N-dimethylamino benzoylformaldoxime; Anthraquinone classes such as 2-methylanthraquinone, 1-chloroanthraquinone and 2-amyl anthraquinone; 2,4-dimethyl thioxanthone, 2,4-diethyl thioxanthone, 2-clopenthixal ketone and 2, thioxanthene ketones such as 4-di-isopropyl thioxanthone; Ketal classes such as methyl phenyl ketone dimethyl ketal and benzyl dimethyl ketal; Benzophenone, methyldiphenyl ketone, 4,4 '-dichloro benzophenone, 4,4 '-two diethylamino benzophenone, Michler's keton (Michler ' s ketone) and 4-benzoyl-4 '-benzophenones such as methyldiphenyl base sulfide; And 2,4,6-trimethylbenzoyl diphenyl phosphine oxide etc.
(C) composition can use separately, also can two kinds or more kinds of and usefulness.
In (C) composition, can as required and use photosensitizers.As photosensitizers, can list N, N-dimethylamino ethyl benzoate, N, N-dimethylamino M-nitro benzoic acid isopentyl ester, triethylamine and trolamine etc.
Preferred blending ratio as (C) composition is, with respect to (A) composition and (B) total amount 100 mass parts of composition, maybe when being mixed with the compound that contains unsaturated group described later, with respect to (A) composition, (B) composition with contain total amount 100 mass parts of the compound of unsaturated group, be preferably 0.05～12 mass parts, more preferably 0.1～5 mass parts.
In composition of the present invention, can mix as required except (A) composition and (B) compound that contains unsaturated group the composition.
Contain the compound of unsaturated group as this; can list for example (methyl) vinylformic acid phenoxy ethyl; (methyl) ethoxy ethoxyethylacrylate; N-vinyl caprolactone; acryloyl morpholine; (methyl) glycidyl acrylate; (methyl) vinylformic acid-2-hydroxyl ethyl ester; (methyl) vinylformic acid-2-hydroxypropyl acrylate; single (methyl) vinylformic acid-1; the 4-butanediol ester; two (methyl) vinylformic acid-1; 6-hexylene glycol ester; diacrylate nonanediol ester; two (methyl) vinylformic acid gathers the glycol ester; (methyl) vinylformic acid-2-hydroxyl-3-phenoxy group propyl ester; (methyl) vinylformic acid tribromophenyl; 2; two (4-(methyl) acryloxy ethoxyl phenenyl) propane of 2-; 2; two (4-(methyl) the acryloxy diethoxy phenyl) propane of 2-; 2, two (4-(methyl) the acryloxy triethoxy phenyl) propane of 2-; two (methyl) vinylformic acid glycol ester; (methyl) vinylformic acid tribromophenoxy ethyl ester; three (methyl) vinylformic acid trihydroxymethylpropanyl ester; four (methyl) vinylformic acid pentaerythritol ester; two (methyl) acrylate of bisphenol A type epoxy resin; poly-(methyl) acrylate of various polyurethane polyureas (methyl) acrylate and polyester etc.
The blending ratio that contains the compound of unsaturated group preferably is the scope of 0～50 quality % in composition.
Except mentioned component, hybrid pigment, dyestuff, foam preventer, flow agent, mineral filler, organic filler and photostabilizer, antioxidant and UV light absorber etc. as required.In addition, also can add small amount of antioxidant, photostabilizer, UV light absorber and polymerization retarder etc. as required.
In order to be cured further, also can be in composition of the present invention the mixture heat polymerization starter, behind the irradiation active energy ray, composition is heated.
As thermal polymerization, can use all cpds, be preferably organo-peroxide and azo-initiator.
Object lesson as organo-peroxide, can list 1,1-bis(t-butylperoxy)-2-methylcyclohexane, 1, two (the uncle's hexyl peroxies)-3 of 1-, 3, the 5-trimethyl-cyclohexane, 1, two (the uncle's hexyl peroxy) hexanaphthenes of 1-, 1,1-bis(t-butylperoxy)-3,3, the 5-trimethyl-cyclohexane, 1, the 1-bis(t-butylperoxy) cyclohexane, 2,2-two (4,4-two (butyl peroxy) cyclohexyl) propane, 1,1-bis(t-butylperoxy) cyclododecane, uncle's hexyl peroxy isopropyl base monocarbonate, the t-butyl peroxy toxilic acid, tert-butyl hydroperoxide-3,5,5-tri-methyl hexanoic acid ester, t-butyl peroxy-laurate, 2,5-dimethyl-2,5-two (toluoyl peroxide) hexane, t-butyl peroxy sec.-propyl monocarbonate, t-butyl peroxy-2-ethylhexyl monocarbonate, the own ester of benzoyl hydroperoxide uncle, 2,5-dimethyl-2,5-two (benzoyl peroxy) hexane, tert-butyl peroxy acetate, 2,2-bis(t-butylperoxy) butane, t-butyl per(oxy)benzoate, 4,4-bis(t-butylperoxy) n-butyl pentanoate, two (t-butylperoxy) isophthalic ester, α, α '-bis(t-butylperoxy) diisopropyl benzene, dicumyl peroxide, 2,5-dimethyl-2,5-two (t-butylperoxy) hexane, the tert-butyl peroxide cumyl, di-t-butyl peroxide, p-menthane hydroperoxide, 2,5-dimethyl-2,5-two (t-butyl peroxy)-3-hexin, the hydroperoxidation diisopropylbenzene(DIPB), the tert-butyl peroxide trimethyl silyl, hydroperoxidation-1,1,3, the 3-tetramethyl butyl, cumene hydroperoxide, hydroperoxidation uncle's hexyl and t-butyl hydroperoxide etc.
As the object lesson of azo compound, can list 1,1 '-azo two (hexanaphthene-1-nitrile), 2-(formamyl azo) isopropyl cyanides, 2-phenylazo-4-methoxyl group-2,4-methyl pentane nitrile, azo two uncle's octanes and azo two uncle's butane etc.
These compounds can use separately, also can two kinds or more kinds of and usefulness.In addition, organo-peroxide also can be by forming redox reaction with the reductive agent combination.
4. actinic-energy-ray-curable composition for optical material
Among the present invention, must contain above-mentioned (A) composition and (B) composition.
(A) composition and (B) components in proportions be, with (A) composition and (B) total amount of composition be benchmark, (A) composition be 10～90 quality % and (B) composition be 90～10 quality %, preferred (A) composition be 30～90 quality % and (B) composition be 70～10 quality %.If (A) components in proportions then can not obtain desirable specific refractory power less than 10 quality %; On the other hand, if (A) components in proportions surpasses 90 quality %, then sometimes at room temperature composition can become solid, aspect operability, have problems.
Composition of the present invention can stir above-mentioned (A) composition other composition with (B) composition and adding as required, mix and make according to ordinary method.
When (A) composition or (C) composition is solid, also can heat after stirring, mixing as required, preferred Heating temperature is 50～100 ℃.
Manufacture method as the optical material that uses the present composition, can be according to ordinary method, for example can list composition coating or be injected into and have in regulation shape framed, the square from it as required then transparency carrier of placing, the irradiation active energy ray solidifies composition, takes out the method for cured article etc. then from template.
As active energy ray, can list electron rays, visible light and ultraviolet ray etc.Wherein, owing to do not need special device and simple, preferred visible light or ultraviolet ray.As UV irradiation equipment, can list high pressure mercury vapour lamp etc.
The irradiation dose of active energy ray and irradiation time can suitably be set according to employed composition and use thereof.
In the composition of the present invention, can obtain to have specific refractory power (25 ℃) be generally more than 1.59 or above, be preferably 1.60 or the cured article of above such high refractive index.In addition, the transparency of this cured article is also good.
Like this, the cured article of composition of the present invention because specific refractory power is high and have the transparency, can be used for various optical materials such as lens such as Fresnel lens, biconvex lens and prismatic lens and plastic lens.
As lens, say in further detail, can list purposes such as video projector (videoprojector), projection TV and liquid-crystal display.
The example that uses composition of the present invention to make lens is described.
When making the thin lens of Film Thickness Ratio, composition of the present invention be coated on have being called in pressing mold framed of target lens shape, the layer of said composition is set, and on this layer bonding transparency carrier.
Then,, composition is solidified, it is stripped down from mould from transparency carrier one side irradiation active energy ray.
On the other hand, when making the thicker lens of Film Thickness Ratio,, inject composition of the present invention having between the framed and transparency carrier of target lens shape.
Then,, composition is solidified, then, it is stripped down from mould from transparency carrier one side irradiation active energy ray.
As above-mentioned transparency carrier, be preferably resin substrate, as object lesson, can use laminar materials such as methacrylic resin, polycarbonate resin, methyl methacrylate-styrene resin and styrene resin.
As above-mentioned framed, its material had no particular limits, but for example can list resins such as metal such as yellow copper and mickel and Resins, epoxy.From long viewpoint of framed life-span, be preferably metal mould.
Below, the example that uses composition of the present invention to make plastic lens is described.
For example, can list that composition of the present invention is injected one side at least is transparent bright finished framed, the irradiation active energy ray solidifies it, again by carrying out method that the demoulding makes etc.
Framed as in this situation, can list make up with glass, plastics or two bright finished templates that they are combined, with the packing ring of thermoplastic resin systems such as plasticized vinylchlorid and ethylene-vinyl acetate copolymer and other the instrument that two templates is carried out matched moulds etc. and constitute framed etc.
This moment, the irradiation of active energy ray can be carried out on the single or double of template.In addition, also irradiation active energy ray and heating can be made up.
Composition of the present invention, operability at room temperature is good, prepared cured article specific refractory power height and light transmittance might as well, and can become the material of the low excellent size stability of water-intake rate.Therefore, composition of the present invention goes for requiring the optical component of the lens of high refractive index, high light line transmissivity and dimensional stability etc. and plastic lens etc.
Embodiment
In the composition of the present invention, must contain (A) composition 90～10 quality % and (B) composition 90～10 quality %.As (A) composition, for the specific refractory power height of the cured article that makes composition, preferred R
1And R
3It all is the diacrylate of hydrogen atom.As composition, preferably contain (C) composition.
In addition, the present invention has the framed of regulation shape, the manufacture method of shining the optical material of active energy ray then with above-mentioned composition coating or injection.
Below, enumerate embodiment and comparative example, the present invention is carried out specific description more.
Embodiment and comparative example
Each composition shown in the table 1 is stirred, mixes according to ordinary method, in remaining 80 ℃ drying machine in advance,, thereby be adjusted into ultraviolet-curable composition with 15 minutes Photoepolymerizationinitiater initiater heating for dissolving with solid state.
At room temperature the composition that makes is coated on the OPP film with thickness 30 μ m with metering bar coater.Being under 10m/ minute the condition in line speed, is that 10cm, power are that the high pressure mercury vapour lamp of 80W/cm shines twice ultraviolet ray to it with the lamp height, makes its curing.
The cured article that makes is estimated according to following method.These the results are shown in the table 2.
(1) operability
Estimate the easy degree of treatment compositions when making cured article.With under the room temperature be liquid be set at zero, will be being set at of solid or paste *.
(2) specific refractory power
Measure the specific refractory power (observed value of the sodium D-line under using 25 ℃) of cured article with the Abbe refractometer DR-M2 of ァ go Co., Ltd. system.
(3) light transmittance
Measure the light transmittance of the cured article under the wavelength 400nm with the Japanese beam split system V-550 of Co., Ltd..
(4) water-intake rate
Place resin board on four angles of glass plate, forming thick is the empty part of 0.4mm.The composition that makes is filled up this sky part, place glass plate then.
Under condition same as described above to its irradiation ultraviolet radiation.After the curing, remove sheet glass, obtain the thin slice of the cured article of the thick 0.4mm of being.
The cured article that makes is cut into 5cm * 5cm, and it as test film.
With this test film in nitrogen in 210 ℃ of down heating 1 hour, make the cured article complete drying after, in moisture eliminator, place cooling after, weighing test film (W1).Then this test film be impregnated in 80 ℃ the distilled water 20 hours, wipe the water on test film surface after the taking-up lightly and carry out weighing (W2), calculate water-intake rate with following formula.
Water-intake rate (%)=100 * (W2-W1)/W1
[table 1]
The following meaning is represented in abbreviation in the table 1.
BAEPS: two (4-acryloxy ethoxyl phenenyl) sulfide
O-PPA: vinylformic acid o-phenyl phenyl ester
P-PPA: vinylformic acid p-cumyl phenyl ester
M-211B: 4 moles of modification diacrylates of bisphenol-A epoxy ethane, the system ァ ロ ニ ッ of Toagosei Co., Ltd Network ス M-211B
M-400: the mixture of five vinylformic acid dipentaerythritol ester and six vinylformic acid dipentaerythritol ester, the system ァ ロ ニ ッ of Toagosei Co., Ltd Network ス M-400
POA: vinylformic acid phenoxy ethyl
The acrylate of 1 mole of affixture of TO-1463:o-phenylphenol oxyethane, the system ァ ロ ニ ッ of Toagosei Co., Ltd Network ス TO-1463
The Irg184:1-hydroxycyclohexylphenylketone, Ciba Specialty Chemicals corporate system Irgacure184
[table 2]
It is evident that from table 2 operability of composition of the present invention is good, the specific refractory power of its cured article is 1.59 or above high refractive index, and light transmittance might as well, water-intake rate is also low.
On the other hand, though contain (A) composition, when containing the composition (comparative example 1) that has only a phenyl and the vinylformic acid phenoxy ethyl different in the molecule, can not make the low cured article of specific refractory power height and water-intake rate with (B) composition when using.In addition, only use in the composition (comparative example 2) of (A) composition,,, can not make cured article so operability is poor owing to be solid at room temperature.In addition,, do not contain the composition (comparative example 3 and comparative example 4) of (A) composition, can not make the low cured article of specific refractory power height and water-intake rate though contain (B) composition.In addition, use different with (B) the of the present invention composition unitary compositions of epoxy alkyl (comparative example 5 and comparative example 6) that have,, can not make the low cured article of water-intake rate though optics rerum naturas such as operability and specific refractory power are good.
Application examples (manufacturing of lens)
The composition that use is made by embodiment 1～embodiment 8, injection has in the mould of lens shape, and the side is lived with the methacrylate resin plate holder of transparency carrier from it.
Under condition same as described above, composition is solidified.
From mould, take out the cured article after solidifying, make target shape, thereby can obtain the good lens of aforesaid optics rerum natura.
Composition of the present invention, as actinic-energy-ray-curable composition for optical material, go for being optical component representative, that require high refractive index and high light line transmissivity with lens such as the Fresnel lens that uses in video projector, projection TV and the liquid-crystal display etc. and biconvex lens and plastic lens etc.
Claims (10)
1. actinic-energy-ray-curable composition for optical material, it is characterized in that, contain two (methyl) acrylate (A) of useful following general formula (1) expression and with list (methyl) acrylate of following general formula (2) expression and/or list (methyl) acrylate of representing with following general formula (3) (B), and with (A) composition and (B) total amount of composition as benchmark, contain (A) composition of 10～90 quality % and (B) composition of 90～10 quality %
In the formula (1), R
1And R
3Represent hydrogen atom or methyl respectively independently; R
2And R
4Represent hydrogen atom, methyl or ethyl respectively independently; R
5～R
8Represent hydrogen atom, methyl or bromine atoms respectively independently; 1 and m represent 1～6 integer respectively independently,
In the formula (2), R
9Expression hydrogen atom or methyl,
In the formula (3), R
10Expression hydrogen atom or methyl.
2. actinic-energy-ray-curable composition for optical material according to claim 1, wherein, described two (methyl) acrylate (A) is R in described general formula (1)
1And R
3It all is the diacrylate of hydrogen atom.
3. actinic-energy-ray-curable composition for optical material according to claim 1 is characterized in that also containing Photoepolymerizationinitiater initiater (C).
4. actinic-energy-ray-curable composition for optical material according to claim 1, wherein, R
2And R
4Be hydrogen atom.
5. actinic-energy-ray-curable composition for optical material according to claim 1, wherein, (A) composition is two (4-methacryloxy ethoxyl phenenyl) sulfide, two (4-acryloxy ethoxyl phenenyl) sulfide, two (4-methacryloxy diethoxy phenyl) sulfide, two (4-acryloxy diethoxy phenyl) sulfide, two (4-methacryloxy triethoxy phenyl) sulfide, two (4-acryloxy triethoxy phenyl) sulfide, two (4-methacryloxy diethoxy-3-aminomethyl phenyl) sulfide, two (4-acryloxy diethoxy-3-aminomethyl phenyl) sulfide, two (4-methacryloxy oxyethyl group-3-bromophenyl) sulfide, two (4-acryloyl-oxy base oxethyl-3-bromophenyl) sulfide, two (4-methacryloxy diethoxy-3-bromophenyl) sulfide or two (4-acryloxy diethoxy-3-bromophenyl) sulfide.
6. actinic-energy-ray-curable composition for optical material according to claim 1, wherein, list (methyl) acrylate of representing with general formula (2) is the adjacent phenyl phenyl ester of (methyl) vinylformic acid.
7. actinic-energy-ray-curable composition for optical material according to claim 1, it contains (A) composition of 30～90 quality % and (B) composition of 70～10 quality %.
8. the manufacture method of an optical material, it comprises:
With the composition coating of claim 1～7 described in any one or be injected into the operation that has in regulation shape framed;
After coating or injecting, the irradiation active energy ray is so that described composition solidified operation; And
After described composition solidifies, the operation that cured article is taken out from mould.
9. optical material, it solidifies the described actinic-energy-ray-curable composition for optical material of claim 1 and obtains by the active energy ray irradiation.
10. optical material according to claim 9, it is lens or plastic lens.
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| JP2003378898 | 2003-11-07 | ||
| JP378898/2003 | 2003-11-07 | ||
| JP378904/2003 | 2003-11-07 |
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| CN100384895C true CN100384895C (en) | 2008-04-30 |
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| US9708424B2 (en) | 2011-09-27 | 2017-07-18 | Kaneka Corporation | (Meth)acryloyl-terminated polyisobutylene polymer, method for producing the same, and active energy ray-curable composition |
| WO2013047314A1 (en) | 2011-09-27 | 2013-04-04 | 株式会社カネカ | (meth)acryloyl-terminated polyisobutylene polymer, method for producing same, and active energy ray-curable composition |
| US9260554B2 (en) | 2012-07-12 | 2016-02-16 | Showa Denko K.K. | Copolymer, monomer composition, resin solution, and resin film |
| CN107556443A (en) * | 2017-09-30 | 2018-01-09 | 宝鸡圭彬光电设备有限公司 | A kind of wear-resisting optical material and preparation method thereof |
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| JPH01180854A (en) * | 1988-01-14 | 1989-07-18 | Canon Inc | Acrylic acid ester for optical use |
| JPH04202308A (en) * | 1990-11-30 | 1992-07-23 | Mitsubishi Rayon Co Ltd | Composition for plastic lens |
| JPH07268045A (en) * | 1994-03-29 | 1995-10-17 | Mitsubishi Rayon Co Ltd | Plastic lens molding composition and plastic lens produced therefrom |
| JPH08208775A (en) * | 1995-02-07 | 1996-08-13 | Nippon Kayaku Co Ltd | Resin composition, composition for lens and cured material thereof |
| JP2002293826A (en) * | 2001-03-28 | 2002-10-09 | Toagosei Co Ltd | Composition for forming active energy ray-curable type resin sheet |
| WO2003064535A1 (en) * | 2002-01-25 | 2003-08-07 | Sumitomo Bakelite Co., Ltd. | Transparent composite composition |
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- 2004-11-05 CN CNB2004800325510A patent/CN100384895C/en not_active Expired - Fee Related
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH01180854A (en) * | 1988-01-14 | 1989-07-18 | Canon Inc | Acrylic acid ester for optical use |
| JPH04202308A (en) * | 1990-11-30 | 1992-07-23 | Mitsubishi Rayon Co Ltd | Composition for plastic lens |
| JPH07268045A (en) * | 1994-03-29 | 1995-10-17 | Mitsubishi Rayon Co Ltd | Plastic lens molding composition and plastic lens produced therefrom |
| JPH08208775A (en) * | 1995-02-07 | 1996-08-13 | Nippon Kayaku Co Ltd | Resin composition, composition for lens and cured material thereof |
| JP2002293826A (en) * | 2001-03-28 | 2002-10-09 | Toagosei Co Ltd | Composition for forming active energy ray-curable type resin sheet |
| WO2003064535A1 (en) * | 2002-01-25 | 2003-08-07 | Sumitomo Bakelite Co., Ltd. | Transparent composite composition |
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| CN1875041A (en) | 2006-12-06 |
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