CN103562272B - Curable composition and adhesive for optical applications - Google Patents
Curable composition and adhesive for optical applications Download PDFInfo
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- CN103562272B CN103562272B CN201280019915.6A CN201280019915A CN103562272B CN 103562272 B CN103562272 B CN 103562272B CN 201280019915 A CN201280019915 A CN 201280019915A CN 103562272 B CN103562272 B CN 103562272B
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/30—Low-molecular-weight compounds
- C08G18/38—Low-molecular-weight compounds having heteroatoms other than oxygen
- C08G18/3855—Low-molecular-weight compounds having heteroatoms other than oxygen having sulfur
- C08G18/3876—Low-molecular-weight compounds having heteroatoms other than oxygen having sulfur containing mercapto groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/08—Processes
- C08G18/16—Catalysts
- C08G18/22—Catalysts containing metal compounds
- C08G18/24—Catalysts containing metal compounds of tin
- C08G18/244—Catalysts containing metal compounds of tin tin salts of carboxylic acids
- C08G18/246—Catalysts containing metal compounds of tin tin salts of carboxylic acids containing also tin-carbon bonds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
- C08G18/76—Polyisocyanates or polyisothiocyanates cyclic aromatic
- C08G18/7614—Polyisocyanates or polyisothiocyanates cyclic aromatic containing only one aromatic ring
- C08G18/7628—Polyisocyanates or polyisothiocyanates cyclic aromatic containing only one aromatic ring containing at least one isocyanate or isothiocyanate group linked to the aromatic ring by means of an aliphatic group
- C08G18/7642—Polyisocyanates or polyisothiocyanates cyclic aromatic containing only one aromatic ring containing at least one isocyanate or isothiocyanate group linked to the aromatic ring by means of an aliphatic group containing at least two isocyanate or isothiocyanate groups linked to the aromatic ring by means of an aliphatic group having a primary carbon atom next to the isocyanate or isothiocyanate groups, e.g. xylylene diisocyanate or homologues substituted on the aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J175/00—Adhesives based on polyureas or polyurethanes; Adhesives based on derivatives of such polymers
- C09J175/04—Polyurethanes
Abstract
Provided is a curable composition which has a high refractive index and also has simultaneously the capabilities required of adhesives for optical applications: light-curability, low shrinkage, colorless transparency, and viscosity suitable for operations. This invention provides the curable composition containing polythiourethane oligomers (component A) obtained by reacting polyols and polyisocyanates, an episulfide compound (component B) and a photobase generator (component C).
Description
Technical field
The present invention relates to as the suitable solidification compound of the optics caking agent used when making composite optic element.
Background technology
The Photocurable compositions such as acrylic compound are widely used as caking agent when making optical element.For caking agent, adaptation, light solidified, physical strength, weather resistance and optical characteristics are fundamental property, but in recent years along with the multifunction of optical element, specific refractory power becomes important performance.Particularly the high refractive index of caking agent is expected high due to the degree of freedom expansion of optical design.As using the purposes example with the caking agent of high refractive index, can list formed by the bonding of two pieces of lens achromatic lens (achromat lens), by glass and the compound of resin form mix the prism etc. that (hybrid) type non-spherical lens, colour splitting prism etc. form complicated shape.For the caking agent used in these purposes, not only require high specific refractory power, certainly also require adaptation, light solidified, colorless transparency, be suitable for these performances of viscosity of operation.
As the compound with high refractive index, find the episulfide (patent documentation 1 ~ 4) containing sulphur atom in many molecular structures with high density.Such as the specific refractory power of the cured article of two (2,3-epithiopropyl) thioether is 1.70.This episulfide, because viscosity is low, easily can inject mould, is therefore suitable for the making of the formed bodys such as glasses lens.But assuming that when using as caking agent, caking agent sagging or flowing when viscosity is too low, when boning, adherend offsets and has problems in workability.In addition, usual episulfide is large owing to solidifying adjoint contraction, becomes the reason that adaptation reduces when therefore using as caking agent.
Prior art document
Patent documentation
Patent documentation 1: Japanese Unexamined Patent Publication 9-71580 publication
Patent documentation 2: Japanese Unexamined Patent Publication 9-110979 publication
Patent documentation 3: Japanese Unexamined Patent Publication 9-255781 publication
Patent documentation 4: Japanese Unexamined Patent Publication 2001-163874 publication
Summary of the invention
the problem that invention will solve
Therefore, the object of the invention is to, provide and there is high specific refractory power, and also have light solidified, low-shrinkage, colorless transparency concurrently, be suitable for the solidification compound of these performances required as optics caking agent of viscosity of operation.
for the scheme of dealing with problems
The present inventor etc. have carried out to solve the problem in depth studying, found that, solidification compound containing polythiourethane oligopolymer (A composition), episulfide (B component) and Photobase generator (C composition) that polythiol and polyisocyanates are obtained by reacting, there is as caking agent the viscosity being suitable for workability, and it is little to solidify adjoint contraction, be therefore suitable as optics caking agent.Based on above discovery, complete the present invention.
the effect of invention
According to the present invention, can provide and there is high specific refractory power, and also have light solidified, low-shrinkage, colorless transparency concurrently, be suitable for these solidification compounds as the performance of optics caking agent of viscosity of operation.
Embodiment
Solidification compound of the present invention contains polythiourethane oligopolymer (A composition), episulfide (B component) and the Photobase generator (C composition) that polythiol and polyisocyanates be obtained by reacting and forms.
First the manufacture method of polythiourethane oligopolymer (A composition) is described.
The polythiol becoming the raw material of polythiourethane oligopolymer refers in a part the compound with two or more thiol group, can be any one in straight-chain, branched, ring-type.When the high refractive indexization particularly pursuing solidification compound and the viscosity being suitable for workability, be preferably the compound shown in following general formula (1) ~ (3).
(in formula (1), p1 and p2 represents the integer of 0 ~ 1 independently of one another, X
1~ X
8represent hydrogen atom or methyl mercaptan base independently of one another.)
(in formula (2), q represents the integer of 0 ~ 3, R
1represent that simple key or carbonatoms are the alkylidene group of 1 ~ 3.)
(in formula (3), r represents the integer of 0 ~ 3, R
2represent that carbonatoms is the alkylidene group of 1 ~ 3)
As the example of the compound shown in general formula (1), can 1 be listed, 5-dimercapto-3-thia pentane, 2-mercapto methyl-1, 5-dimercapto-3-thia pentane, 2, two (mercapto methyl)-1 of 4-, 5-dimercapto-3-thia pentane, 4-mercapto methyl-1, 8-dimercapto-3, 6-dithia octane, 4, two (mercapto methyl)-1 of 8-, 11-dimercapto-3, 6, 9-tri-thia undecane, 4, two (mercapto methyl)-1 of 7-, 11-dimercapto-3, 6, 9-tri-thia undecane, 5, two (mercapto methyl)-1 of 7-, 11-dimercapto-3, 6, 9-tri-thia undecane etc., as the example of compound general formula (2) Suo Shi, can 2 be listed, 5-dimercapto-1, 4-dithian, 2, 5-dimercapto methyl isophthalic acid, 4-dithian, 2, 5-dimercapto ethyl-1, 4-dithian etc., as the example of compound general formula (3) Suo Shi, xylylene two mercaptan etc. can be listed.As the poly-thiol compound beyond compound general formula (1) ~ (3) Suo Shi, ethylene glycol bis (3-mercaptopropionic acid ester), trimethylolpropane tris (3-mercaptopropionic acid ester), tetramethylolmethane four (3-mercaptopropionic acid ester), phenylene dimercaptan, benzylidene two mercaptan etc. can be listed.
The polyisocyanates becoming the raw material of polythiourethane oligopolymer refers in a part the compound with two or more isocyanate group, can be any one in straight-chain, branched, ring-type.As the example of this polyisocyanates, an eylylene diisocyanate, 1 can be listed, 3-two (2-isocyano-2-propyl group) benzene, tolylene diisocyanate, ditan-4,4 '-vulcabond, 1,3-two (2-isocyano-2-propyl group) hexanaphthene, isophorone diisocyanate, dicyclohexyl methyl hydride-4,4 '-vulcabond, hexamethylene diisocyanate, trimethyl hexamethylene diisocyanate, three (6-isocyano hexyl) isocyanuric acid esters etc.They can be used alone or combine two or more use.When particularly pursuing the high refractive index of solidification compound and low yellow, preferred polyisocyanates be between eylylene diisocyanate, 1, two (2-isocyano-2-propyl group) benzene of 3-, 1,3-two (2-isocyano-2-propyl group) hexanaphthene, isophorone diisocyanate.
About the reaction of polythiol and polyisocyanates, such as, when product is dipolymer, carry out according to following reaction formula.
(in formula, R and R ' represents organic group, a and b represents the integer of more than 1).
Because thiol group and isocyanate group are with 1 to 1 molar reactive, the mol ratio of thiol group and isocyanate group more generates the larger polythiourethane oligopolymer of molecular weight close to 1.About the ratio of mixture of polythiol and polyisocyanates, relative to 1 molar sulphur alcohol radical, isocyanate group is preferably in the scope of 0.2 ~ 0.95 mole, is more preferably in the scope of 0.4 ~ 0.95 mole.When isocyanate group is less than 0.2 mole, the transformation efficiency of thiol group is too low and impracticable, and during more than 0.95 mole, the isocyanate group of remained unreacted, so not preferred.
The reaction of polythiol and polyisocyanates is carried out heating to carry out under existing in the presence of a catalyst or not, is preferably the method using catalyzer.As catalyzer, the tin compound such as dibutyl tin laurate, dibutyl dichloro tin can be listed, the basic cpd such as amine, phosphine.About the consumption of catalyzer, relative to polythiol 100 weight part of raw material, be preferably in the scope of 0.01 ~ 10 weight part, be more preferably in the scope of 0.1 ~ 1.0 weight part.
The reaction of polythiol and polyisocyanates can be carried out under the existence of episulfide (B component).The reaction of polythiol and polyisocyanates can use solvent as required.When using solvent, distillation is needed to remove the rear operation of solvent.Temperature of reaction is not particularly limited, but is preferably in the scope of 0 ~ 100 DEG C, also can observing response carry out situation raised temperature lentamente on one side.Reaction times, owing to depending on the various condition such as ratio of mixture, temperature of reaction of the kind of raw material, polythiol and polyisocyanates, can not generally specify, but the polyisocyanates of the straight not remained unreacted of reaction.
Then solidification compound of the present invention is described.
Solidification compound of the present invention contains aforementioned polythiourethane oligopolymer (A composition), episulfide (B component) and Photobase generator (C composition) and forms.
Episulfide (B component) refers in a part the compound with more than one episulfide.When particularly pursuing the high refractive index of solidification compound, be preferably the compound shown in following general formula (4).
(in formula (4), m is the integer of 0 ~ 6, and n is the integer of 0 ~ 4, R
3and R
4be hydrogen atom or carbonatoms be independently of one another the alkyl of 1 ~ 10, R
5, R
6to be carbonatoms be independently of one another 1 ~ 10 alkylidene group.)
As the example of the episulfide shown in general formula (4), two (2,3-epithiopropyl) thioethers etc. can be listed.
General formula (4) although shown in episulfide to solidify adjoint contraction large, by with the copolymerization of polythiourethane oligopolymer, can suppress to solidify adjoint contraction.In addition, general formula (4) although shown in the general viscosity of episulfide low, by mixing with polythiourethane oligopolymer, adjust to the viscosity of workability excellence.
About the viscosity of solidification compound, when supposing to use as caking agent, when viscosity is too low, caking agent sagging or flowing, bond time substrate skew and not preferred.In addition, when viscosity is too high, be difficult to discharge, the coating of carrying out caking agent, or enter bubble, so not preferred during bonding.The viscosity being suitable for workability alleged in the present invention is owing to depending on the use-pattern of the caking agent of coating process, adhesive method and so on, can not generally specify, but be preferably in the scope of 500 ~ 20000mPas, be more preferably in the scope of 500 ~ 10000mPas.
For the content of polythiourethane oligopolymer, relative to 100 weight part solidification compounds, be preferably in the scope of 10 ~ 70 weight parts, be preferably in further in the scope of 20 ~ 60 weight parts.Polythiourethane oligopolymer containing quantity not sufficient 10 weight part time, the effect of high viscosity, lower shrinkage diminishes, and reduces, so not preferred more than the toughness of cured article during 70 weight part.
Photobase generator (C composition) refers to by active ray the compound of photodissociation, generation alkali.Particularly the polymerization of episulfide is owing to promoting by the amidine such as DBN (diazabicyclo-nonene), DBU (diazabicycloundecene), therefore preferably produces the Photobase generator of these alkali.Specifically, 1, the 3-diamines (left side of following formula (6)) etc. replaced by arylalkyl recorded can be listed in amidine (amidinium) ketone (left side of following formula (5)) of formation four aromatic yl acid salt recorded in Japanese Unexamined Patent Application Publication 2001-513765, Japanese Unexamined Patent Application Publication 2005-511536.They separately or can mix two or more use.About the addition of Photobase generator, relative to 100 weight part solidification compounds, be preferably in the scope of 0.01 ~ 10 weight part, be more preferably in the scope of 0.1 ~ 5 weight part.
(in formula (5), Ar
1phenyl, xenyl, naphthyl, phenanthryl, anthryl, pyrenyl, 5,6,7,8-tetrahydrochysene-2-naphthyl, 5,6,7,8-tetrahydrochysene-1-naphthyl, thienyl, benzo [b] thienyl, naphtho-[2,3-b] thienyl, thianthrenyl, dibenzofuran group, benzopyranyl, xanthenyl, thioxanthene base, phenoxathiinyl, terphenyl, stilbene radicals or fluorenyl, these groups are not for replace or by C1 ~ C18 alkyl, C3 ~ C18 thiazolinyl, C3 ~ C18 alkynyl, C1 ~ C18 haloalkyl, NO
2, OH, CN, OR
7, SR
8, C (O) R
9, C (O) OR
10or halogen atom replaces once, R
7~ R
10hydrogen or C1 ~ C18 alkyl independently of one another.)
(in formula (6), Ar
2be phenyl, naphthyl, anthryl or anthraquinonyl, these groups are not for replace or by C1 ~ C4 alkyl, C2 ~ C4 thiazolinyl, NO
2, CN, OR
11, SR
12, C (O) R
13, C (O) OR
14or halogen atom replaces once, R
11~ R
14hydrogen or C1 ~ C4 alkyl independently of one another, R
15hydrogen or C1 ~ C6 alkyl.)
In addition, except Photobase generator, also photosensitizers can be contained.By adding photosensitizers, the photodissociation of Photobase generator is accelerated, and can shorten the set time of Photocurable composition.As the concrete example of photosensitizers, benzophenone, thioxanthene ketone, Anthraquinones, camphor quinones, dibenzoyl class, tetramethyldiaminobenzophenone class, anthracene class can be listed.They separately or can mix two or more use.About the addition of photosensitizers, relative to 100 weight part solidification compounds, be preferably in the scope of 0.01 ~ 10 weight part, be more preferably in the scope of 0.1 ~ 5 weight part.
In said curing property composition, stopper, polymerization retarder, antioxidant, UV light absorber, silane coupling agent, releasing agent, pigment, dyestuff etc. can be added as required.In addition, can carry out as required filtering, deaeration etc.
Embodiment
By the following examples the present invention is specifically described, but the present invention is not limited by them.It should be noted that, the cure shrinkage in embodiment is calculated by the specific refractory power before and after solidifying according to following calculating formula.
X=(1-d1/d2)×100[%]
R=(n
2-1)/(n
2+2)×M/d
Before and after solidification, R/M is constant, therefore known by above two formulas,
X=[1-{(n1
2-1)/(n1
2+2)}/{(n2
2-1)/(n2
2+2)}]×100[%]
(in formula, X represents cure shrinkage, d represents proportion, d1 represent solidification before proportion, d2 represent solidification after proportion, R represents molar refraction, n represents specific refractory power, n1 represent solidification before specific refractory power, n2 represent solidification after specific refractory power, M represent molecular weight.)
In addition, the viscosity of solidification compound uses circular cone/flat plate-type viscometer DV-II+ (Brookfield Inc.) to measure at temperature 25 DEG C.The specific refractory power of solidification compound and cured film uses Abbérefractometer NAR-3T (ATAGO CO., LTD system) to measure.The transmitance of cured film uses spectrophotometer U-3500 (Hitachi High-Technologies Corporation system), measures under the condition of the thickness 0.25mm of cured film, wavelength 400nm.
Embodiment 1
2,5-dimercapto methyl-Isosorbide-5-Nitrae-dithian 25g, an eylylene diisocyanate 15g and dibutyl tin laurate 0.1g is got, continuously stirring 24 hours at 60 DEG C in 300ml flask.Confirm that the IR of isocyanate group absorbs (2280cm with infrared spectrophotometer
-1) after disappearance; add two (2; 3-epithiopropyl) thioether 60g, the Photobase generator 0.5g (C composition) shown in following structural formula (7) and the 4-benzoyl-4 as sensitizer '-dimethyl diphenyl sulfide 1g, be stirred to evenly.Solidification compound is made according to above step.
By the solidification compound two pieces of sheet glass clamping that have passed through demoulding process, after the distance of 30cm irradiates the light 3 minutes from metal halide lamp (120W/cm), the film that have cured is peeled off by sheet glass.The cured film of thickness 0.25mm is made according to above step.
The physical property of solidification compound and cured film is as shown in table 1.
Embodiment 2 ~ 5
The kind of polythiol, polyisocyanates and episulfide and addition change into the content shown in table 1, in addition the making of being cured property composition and cured film similarly to Example 1.The physical property of solidification compound and cured film is as shown in table 1.
Comparative example 1
Add two (2,3-epithiopropyl) thioether 100g, the Photobase generator 0.5g (C composition) shown in aforementioned structural formula (7) and the 4-benzoyl-4 as sensitizer '-dimethyl diphenyl sulfide 1g, be stirred to evenly.Solidification compound is made according to above step.
Make cured film similarly to Example 1.The physical property of solidification compound and cured film is as shown in table 2.It should be noted that, underscore is drawn for the physical property than embodiment difference.
Comparative example 2
Add 2; 5-dimercapto methyl isophthalic acid; 4-dithian 20g, two (2; 3-epithiopropyl) thioether 80g, the Photobase generator 0.5g (C composition) shown in aforementioned structural formula (7) and the 4-benzoyl-4 as sensitizer '-dimethyl diphenyl sulfide 1g, be stirred to evenly.Solidification compound is made according to above step.
Make cured film similarly to Example 1.The physical property of solidification compound and cured film is as shown in table 2.It should be noted that, underscore is drawn for the physical property than embodiment difference.
[table 1]
Table 1
[table 2]
Table 2
| Comparative example 1 | Comparative example 2 | |
| Polythiol | - | a-1：20 |
| Episulfide | c-1：100 | c-1：80 |
| Viscosity (mPas) | 12 | 17 |
| Cure shrinkage (%) | 12.6 | 12.3 |
| The refractive index n D of cured film | 1.711 | 1.707 |
| The transmitance (%) of cured film | 55 | 94 |
The explanation of abridging in table
(a-1) 2,5-dimercapto methyl-Isosorbide-5-Nitrae-dithian
(a-2) tetramethylolmethane four (3-mercaptopropionic acid ester)
(a-3) xylylene two mercaptan between
(a-4) 1,5-dimercapto-3-thia pentane
(b-1) eylylene diisocyanate between
(b-2) 1,3-two (2-isocyanic ester root-2-propyl group) hexanaphthene
(b-3) 1,3-two (2-isocyanic ester root-2-propyl group) benzene
(b-4) isophorone diisocyanate
(c-1) two (2,3-epithiopropyl) thioether
Claims (5)
1. an optical cement solidification compound, it contains polythiourethane oligopolymer (A composition), episulfide (B component) and Photobase generator (C composition) that polythiol and polyisocyanates are obtained by reacting,
Wherein, more than one for being selected from the group that is made up of following general formula (1), following general formula (2) and following general formula (3) of described polythiol,
In formula (1), p1 and p2 represents the integer of 0 ~ 1 independently of one another, X
1~ X
8represent hydrogen atom or methyl mercaptan base independently of one another,
In formula (2), q represents the integer of 0 ~ 3, R
1represent that simple key or carbonatoms are the alkylidene group of 1 ~ 3,
In formula (3), r represents the integer of 0 ~ 3, R
2represent that carbonatoms is the alkylidene group of 1 ~ 3,
Described Photobase generator (C composition) is the compound shown in following general formula (9),
In formula (9), Ar
2be phenyl, naphthyl, anthryl or anthraquinonyl, these groups are not for replace or by C1 ~ C4 alkyl, C2 ~ C4 thiazolinyl, NO
2, CN, OR
11, SR
12, C (O) R
13, C (O) OR
14or halogen atom replaces once, R
11~ R
14hydrogen or C1 ~ C4 alkyl independently of one another, R
15hydrogen or C1 ~ C6 alkyl,
The viscosity of described optical cement solidification compound is 500 ~ 20000mPas.
2. optical cement solidification compound according to claim 1, wherein, polythiol when reacting about polythiol and polyisocyanates and the ratio of polyisocyanates, relative to 1 molar sulphur alcohol radical, isocyanate group is in the scope of 0.2 ~ 0.95 mole.
3. optical cement solidification compound according to claim 1 and 2, wherein, episulfide (B component) is the compound shown in following general formula (4),
In formula (4), m is the integer of 0 ~ 6, and n is the integer of 0 ~ 4, R
3and R
4be hydrogen atom or carbonatoms be independently of one another the alkyl of 1 ~ 10, R
5and R
6to be carbonatoms be independently of one another 1 ~ 10 alkylidene group.
4. optical cement solidification compound according to claim 3, wherein, the compound shown in general formula (4) is two (2,3-epithiopropyl) thioethers.
5. an optics caking agent, it contains the optical cement solidification compound according to any one of Claims 1 to 4.
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|---|---|---|---|
| JP2011-101441 | 2011-04-28 | ||
| JP2011101441 | 2011-04-28 | ||
| PCT/JP2012/060900 WO2012147709A1 (en) | 2011-04-28 | 2012-04-24 | Curable composition and adhesive for optical applications |
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|---|---|
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| CN103562272B true CN103562272B (en) | 2015-07-08 |
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|---|---|
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| CN (1) | CN103562272B (en) |
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| WO2023063398A1 (en) * | 2021-10-15 | 2023-04-20 | 三井化学株式会社 | Photocurable composition, cured article, laminated body, method for producing cured article, and method for producing lens |
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| JPH11349658A (en) * | 1998-06-11 | 1999-12-21 | Sumitomo Seika Chem Co Ltd | Curable composition and optical material obtained by using the same |
| DE60304935T2 (en) * | 2002-06-04 | 2006-09-21 | Hoya Corp. | Process for the production of plastic lenses and the produced plastic lens |
| JP4765626B2 (en) * | 2003-08-06 | 2011-09-07 | 三菱瓦斯化学株式会社 | Photocurable composition and coating agent composition |
| JP4843955B2 (en) * | 2004-02-16 | 2011-12-21 | 三菱瓦斯化学株式会社 | Photobase generator |
| DE602005002571T2 (en) * | 2004-02-16 | 2008-01-31 | Mitsubishi Gas Chemical Co., Inc. | Photobase generator and curable composition |
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| JP2011038050A (en) * | 2009-08-18 | 2011-02-24 | Mitsubishi Gas Chemical Co Inc | Photo-curable composition, method for curing the same, and cured product thereof |
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| TW201305249A (en) | 2013-02-01 |
| JPWO2012147709A1 (en) | 2014-07-28 |
| WO2012147709A1 (en) | 2012-11-01 |
| CN103562272A (en) | 2014-02-05 |
| JP6230419B2 (en) | 2017-11-15 |
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