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WO2018168233A1 - Composition durcissable, objet durci, élément optique et lentille - Google Patents

Composition durcissable, objet durci, élément optique et lentille Download PDF

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Publication number
WO2018168233A1
WO2018168233A1 PCT/JP2018/003179 JP2018003179W WO2018168233A1 WO 2018168233 A1 WO2018168233 A1 WO 2018168233A1 JP 2018003179 W JP2018003179 W JP 2018003179W WO 2018168233 A1 WO2018168233 A1 WO 2018168233A1
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Prior art keywords
group
curable composition
compound
cured product
atom
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English (en)
Japanese (ja)
Inventor
貴文 中山
直之 師岡
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Fujifilm Corp
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Fujifilm Corp
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Priority to JP2019505755A priority Critical patent/JP6743279B2/ja
Publication of WO2018168233A1 publication Critical patent/WO2018168233A1/fr
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F2/00—Processes of polymerisation
    • C08F2/38—Polymerisation using regulators, e.g. chain terminating agents, e.g. telomerisation
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10—Esters
    • C08F220/20—Esters of polyhydric alcohols or phenols, e.g. 2-hydroxyethyl (meth)acrylate or glycerol mono-(meth)acrylate
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F4/00—Polymerisation catalysts
    • C08F4/28—Oxygen or compounds releasing free oxygen
    • C08F4/32—Organic compounds
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
    • G02B1/04—Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of organic materials, e.g. plastics

Definitions

  • the present invention relates to a curable composition, a cured product, an optical member, and a lens.
  • glass materials have been used for optical members of imaging modules such as cameras, video cameras, camera-equipped mobile phones, videophones, and camera doorphones. Glass materials have been used preferably because they have various optical properties and are excellent in environmental resistance. However, they have the disadvantages that weight reduction and size reduction are not easy, and workability and productivity are poor. On the other hand, the cured resin can be mass-produced and is excellent in workability, and has recently been used for various optical members.
  • Patent Document 1 discloses that a curable composition capable of forming a cured product having a low Abbe number can be obtained by using a compound having a fluorene skeleton and a compound having an aromatic ring condensed ring group. It is disclosed.
  • Patent Document 2 discloses an optical material containing a cage-type polysilsesquioxane derivative having a specific structure, a bifunctional (meth) acrylate having a fluorene structure, and a bifunctional fluorine-containing (meth) acrylate.
  • a resin precursor composition is disclosed.
  • the partial dispersion ratio ( ⁇ g, F) tends to decrease as the Abbe number ( ⁇ d) of the cured product increases, and the Abbe number ( ⁇ d) and the partial dispersion ratio ( ⁇ g, It is known that the value of F) has a negative correlation.
  • a partial dispersion ratio ( ⁇ g, F) higher than the predicted partial dispersion ratio ( ⁇ g, F) in a cured product having a predetermined Abbe number may be required.
  • Patent Documents 1 and 2 a sufficiently high partial dispersion ratio ( ⁇ g, F) in a cured product having a predetermined Abbe number has not been obtained. For this reason, development of the curable composition which can shape
  • the surface shape of the cured product is required to be highly accurate, and the development of a curable composition excellent in mold transferability is also required.
  • the present inventors have a partial dispersion ratio ( ⁇ g, F) that is higher than the partial dispersion ratio ( ⁇ g, F) predicted for a cured product having a predetermined Abbe number.
  • the present invention has been studied for the purpose of providing a curable composition capable of forming a cured product having).
  • the present inventors have also studied for the purpose of providing a curable composition having excellent mold transferability.
  • the concrete means for solving the above problems are as follows.
  • Compound A represented by the following general formula (A): Compound B having at least one fluorine atom and at least one radical crosslinkable group in one molecule; At least one selected from a thermal radical polymerization initiator and a photo radical polymerization initiator; A curable composition comprising:
  • Ar 11 and Ar 12 each independently represent an aryl group containing a benzene ring surrounded by a broken line or a heteroaryl group containing a benzene ring surrounded by a broken line as one of condensed rings;
  • X 1 , Y 1 , X 2 and Y 2 are each independently an oxygen atom, a sulfur atom, a nitrogen atom or a carbon atom, and Z 1 is a 5- to 7-membered aromatic ring together with X 1 —C ⁇ C—Y 1
  • Ar 11 to Ar 14 are each independently a condensed ring group containing an aromatic ring surrounded by a broken line as one of the condensed rings, a group having L 1 as a linking group, a group having L 2 as a linking group, and R 3 to R 6 may be each independently substituted with an aromatic ring surrounded by a broken line, or may be substituted with a condensed ring other than the aromatic ring surrounded by a broken line.
  • a curable composition capable of forming a cured product having a partial dispersion ratio ( ⁇ g, F) higher than an expected partial dispersion ratio ( ⁇ g, F) in a cured product having a predetermined Abbe number.
  • ⁇ g, F partial dispersion ratio
  • ⁇ g, F expected partial dispersion ratio
  • die transferability can be obtained.
  • a numerical range expressed using “to” means a range including numerical values described before and after “to” as a lower limit value and an upper limit value.
  • (meth) acrylate represents acrylate and methacrylate
  • (meth) acryloyl represents acryloyl and methacryloyl.
  • the monomer in the present invention is distinguished from oligomers and polymers, and refers to a compound having a weight average molecular weight of 1,000 or less.
  • the notation that does not indicate substitution and non-substitution includes those having no substituent and those having a substituent.
  • the “alkyl group” includes not only an alkyl group having no substituent (unsubstituted alkyl group) but also an alkyl group having a substituent (substituted alkyl group).
  • the curable composition contains a compound A represented by the general formula (A) described later and a compound B having at least one fluorine atom and at least one radical crosslinkable group in one molecule.
  • the curable composition is molded into a cured product having a partial dispersion ratio ( ⁇ g, F) higher than the predicted partial dispersion ratio ( ⁇ g, F) in the cured product having a predetermined Abbe number. Can do. Also, it exhibits excellent mold transferability.
  • the Abbe number ( ⁇ d) and the partial dispersion ratio ( ⁇ g, F) of the cured product formed from the curable composition are values measured using an Abbe refractometer (manufactured by Kalnew Optical Industry Co., Ltd.). Specifically, the curable composition is poured into a transparent glass mold having a diameter of 10 mm and a thickness of 1 mm and heated at 200 ° C. in an atmosphere having an oxygen concentration of 1% or less to form a cured product (heating step). The Abbe number ( ⁇ d) and the partial dispersion ratio ( ⁇ g, F) are measured for the cured product. The Abbe number ( ⁇ d) and the partial dispersion ratio ( ⁇ g, F) of the cured product are calculated by the following equations.
  • ⁇ d (nd ⁇ 1) / (nF ⁇ nC) ⁇ g
  • F (ng ⁇ nF) / (nF ⁇ nC)
  • nd represents a refractive index at a wavelength of 587.56 nm
  • nF represents a refractive index at a wavelength of 486.13 nm
  • nC represents a refractive index at a wavelength of 656.27 nm
  • ng represents a refractive index at a wavelength of 435.83 nm.
  • the predicted partial dispersion ratio ( ⁇ g, F) is represented by the Abbe number ( ⁇ d) based on the d-line as the horizontal axis and the partial dispersion ratio ( ⁇ g, F) as the vertical axis.
  • the partial dispersion ratio ( ⁇ g, F) on this standard line is there.
  • Glass type A has an Abbe number ( ⁇ d) of 60.49 and a partial dispersion ratio ( ⁇ g, F) of 0.5436.
  • the Abbe number ( ⁇ d) of the glass type B is 36.26
  • the partial dispersion ratio ( ⁇ g, F) is 0.5828.
  • the standard line is a straight line connecting these two points.
  • ⁇ ( ⁇ g, F) is a difference between the partial dispersion ratio ( ⁇ g, F) of the object and the partial dispersion ratio ( ⁇ g, F) on the standard line, and is calculated by the following equation.
  • ⁇ ( ⁇ g, F) Partial dispersion ratio ( ⁇ g, F) of the object ⁇ Partial dispersion ratio ( ⁇ g, F) on the standard line having the same Abbe number ( ⁇ d) as the object It can be said that the higher the value of ⁇ ( ⁇ g, F) calculated by the above formula, the higher the partial dispersion ratio ( ⁇ g, F) than the predicted partial dispersion ratio ( ⁇ g, F).
  • ⁇ ( ⁇ g, F) is preferably 0.040 or more, more preferably 0.046 or more, further preferably 0.060 or more, and 0.080 or more. Is more preferable, and 0.100 or more is particularly preferable.
  • the Abbe number of the cured product formed from the curable composition of the present invention is not particularly limited, but the Abbe number of the cured product is preferably 35 or less, more preferably 30 or less, and 27 More preferably, it is more preferably 25 or less.
  • the curable composition of the present invention can exhibit excellent mold transferability.
  • the mold transferability can be evaluated based on the yield rate by curing 100 curable compositions and molding 100 cured products.
  • a product with fine irregularities (wrinkles) on the surface of the cured product is evaluated as a defective product, and a product with no unevenness is evaluated as a good product.
  • the non-defective rate is preferably 50% or more, more preferably 70% or more, and further preferably 90% or more.
  • the viscosity of the curable composition of the present invention is preferably 20,000 mPa ⁇ s or less, more preferably 15,000 mPa ⁇ s or less, and further preferably 13,000 mPa ⁇ s or less. 000 mPa ⁇ s or less is particularly preferable.
  • the viscosity of the curable composition is preferably 2,000 mPa ⁇ s or more, more preferably 3,000 mPa ⁇ s or more, further preferably 4,000 mPa ⁇ s or more, 000 mPa ⁇ s or more is particularly preferable.
  • a curable composition contains the compound A represented by the following general formula (A).
  • Ar 11 and Ar 12 each independently represent an aryl group containing a benzene ring surrounded by a broken line or a heteroaryl group containing a benzene ring surrounded by a broken line as one of condensed rings.
  • X 1 , Y 1 , X 2 and Y 2 are each independently an oxygen atom, a sulfur atom, a nitrogen atom or a carbon atom
  • Z 1 is a 5- to 7-membered aromatic ring together with X 1 —C ⁇ C—Y 1
  • Z 2 represents 5 to 7 together with X 2 —C ⁇ C—Y 2
  • An atomic group that forms a member aromatic ring and represents an atomic group that includes at least one selected from an oxygen atom, a sulfur atom, a nitrogen atom, and a carbon atom.
  • Ar 13 and Ar 14 each independently represent an arylene group containing an aromatic ring surrounded by a broken line or a heteroarylene group containing an aromatic ring surrounded by a broken line, and at least one of Ar 13 and Ar 14 is other than a phenylene group It is the basis of.
  • R 3 to R 6 each independently represents a substituent
  • q and r are each independently an integer of 0 to 4
  • v is an integer of 0 or more
  • w is an integer of 0 or more
  • L 1 and L 2 each independently represents a single bond, an oxygen atom or a sulfur atom
  • R 11 and R 12 each independently represent an ether bond, an ester bond, a thioether bond, a thioester bond, an amide bond, a carbonate bond and an alkylene.
  • a linking group containing at least one selected from a group or a single bond is represented, and R 21 and R 22 each independently represents a hydrogen atom or a methyl group.
  • Ar 11 to Ar 14 are each independently a condensed ring group containing an aromatic ring surrounded by a broken line as one of the condensed rings, a group having L 1 as a linking group, a group having L 2 as a linking group, and R 3 to R 6 may be each independently substituted with an aromatic ring surrounded by a broken line, or may be substituted with a condensed ring other than the aromatic ring surrounded by a broken line.
  • Ar 11 and Ar 12 each independently represent an aryl group containing a benzene ring surrounded by a broken line or a heteroaryl group containing a benzene ring surrounded by a broken line as one of condensed rings.
  • Ar 11 and Ar 12 are preferably each independently an aryl group containing a benzene ring surrounded by a broken line.
  • the aryl group is preferably an aryl group having 6 to 18 carbon atoms, and an aryl group having 6 to 14 carbon atoms More preferably, it is an aryl group having 6 to 10 carbon atoms.
  • Ar 11 and Ar 12 are particularly preferably each independently a phenyl group composed of only a benzene ring surrounded by a broken line.
  • the heteroaryl group is preferably a heteroaryl group having 9 to 14 ring members. More preferably, it is a heteroaryl group having 9 to 10 ring members.
  • examples of the hetero atom include a nitrogen atom, an oxygen atom, and a sulfur atom.
  • X 1 , Y 1 , X 2 and Y 2 are each independently an oxygen atom, a sulfur atom, a nitrogen atom or a carbon atom. All of X 1 , Y 1 , X 2 and Y 2 may be carbon atoms, and all of X 1 , Y 1 , X 2 and Y 2 may be atoms other than carbon (from oxygen atoms, sulfur atoms and nitrogen atoms). At least one selected).
  • At least a part of X 1 , Y 1 , X 2 and Y 2 is a carbon atom, and a part of X 1 , Y 1 , X 2 and Y 2 is selected from an oxygen atom, a sulfur atom and a nitrogen atom.
  • One kind may be sufficient.
  • Z 1 is an atomic group that forms a 5- to 7-membered aromatic ring with X 1 —C ⁇ C—Y 1 , and an atom containing at least one selected from an oxygen atom, a sulfur atom, a nitrogen atom, and a carbon atom
  • Z 2 represents an atomic group that forms a 5- to 7-membered aromatic ring together with X 2 —C ⁇ CY 2 , and is at least one selected from an oxygen atom, a sulfur atom, a nitrogen atom, and a carbon atom Represents a group of atoms including species.
  • Z 1 and Z 2 are each independently preferably an atomic group containing a carbon atom, and more preferably an atomic group consisting of a carbon atom.
  • Z 1 is preferably an atomic group that forms a 5- or 6-membered aromatic ring together with X 1 —C ⁇ CY 1 , and more preferably an atomic group that forms a 6-membered aromatic ring.
  • Z 2 is preferably an atomic group that forms a 5- or 6-membered aromatic ring together with X 2 —C ⁇ C—Y 2 , and more preferably an atomic group that forms a 6-membered aromatic ring.
  • Ar 13 and Ar 14 each independently represent an arylene group including an aromatic ring surrounded by a broken line or a heteroarylene group including an aromatic ring surrounded by a broken line.
  • the arylene group is preferably an arylene group having 6 to 18 carbon atoms, and an arylene group having 6 to 14 carbon atoms More preferably, it is an arylene group having 6 to 10 carbon atoms.
  • the heteroarylene group is preferably a heteroarylene group having 9 to 14 ring members. More preferably, it is a heteroarylene group having 9 to 10 ring members.
  • examples of the hetero atom include a nitrogen atom, an oxygen atom, and a sulfur atom.
  • At least one of Ar 13 and Ar 14 is a group other than a phenylene group. At least one of Ar 13 and Ar 14 is preferably a condensed ring group containing an aromatic ring surrounded by a broken line, or the aromatic ring surrounded by a broken line is a hetero ring. Among them, at least one of Ar 13 and Ar 14 is more preferably a condensed ring group containing an aromatic ring surrounded by a broken line, and examples of the condensed ring group include naphthylene. In particular, Ar 14 is preferably a condensed ring group containing an aromatic ring surrounded by a broken line.
  • the condensed ring contains a hetero atom, and a nitrogen atom can be illustrated preferably as a hetero atom.
  • Ar 13 and Ar 14 are preferably not the same group. In this case, the other of Ar 13 or Ar 14 is particularly preferably a phenylene group.
  • R 3 to R 6 each independently represents a substituent.
  • the substituent represented by R 3 to R 6 is not particularly limited, and examples thereof include halogen atoms, halogenated alkyl groups, alkyl groups, alkenyl groups, acyl groups, hydroxyl groups, hydroxyalkyl groups, alkoxy groups, aryl groups, and heteroaryls.
  • the substituent represented by R 3 to R 6 is preferably a halogen atom, an alkyl group, an alkoxy group, an aryl group or a cyano group, and is preferably a halogen atom, an alkyl group having 1 to 5 carbon atoms, or an alkoxy group having 1 to 5 carbon atoms. More preferably a phenyl group or a cyano group, and particularly preferably a halogen atom, a methyl group, a methoxy group, a phenyl group or a cyano group.
  • R 3 and R 4 are preferably each independently a methyl group or a methoxy group
  • R 5 is preferably a halogen atom, a methyl group, or a methoxy group
  • R 6 is a halogen atom, a methyl group, or a methoxy group. It is preferably a group or a cyano group.
  • q and r are each independently an integer of 0 to 4, preferably an integer of 0 to 3, and more preferably an integer of 0 to 2.
  • V is an integer of 0 or more, and the maximum number of v is the maximum number of substituents that can be substituted on the ring formed by X 1 —C ⁇ C—Y 1 and Z 1 .
  • v is preferably an integer of 0 to 3, and more preferably an integer of 0 to 2.
  • w is an integer of 0 or more, and the maximum number of w is the maximum number of substituents that can be substituted on the ring formed by X 2 —C ⁇ C—Y 2 and Z 2 .
  • w is preferably an integer of 0 to 3, and more preferably an integer of 0 to 2.
  • all of q, r, v, and w may be 0.
  • the plurality of R 3 may be the same or different, and when r is an integer of 2 to 4, the plurality of R 4 may be the same. May be different.
  • v is an integer of 2 or more, the plurality of R 5 may be the same or different, and when w is an integer of 2 or more, the plurality of R 6 may be the same or different. Good.
  • L 1 and L 2 each independently represents a single bond, an oxygen atom or a sulfur atom.
  • L 1 and L 2 are each independently preferably an oxygen atom or a sulfur atom, and more preferably an oxygen atom.
  • R 11 and R 12 each independently represents a linking group containing at least one selected from an ether bond, an ester bond, a thioether bond, a thioester bond, an amide bond, a carbonate bond and an alkylene group, or a single bond.
  • R 11 and R 12 are each independently a linking group containing at least one selected from an ether bond, an ester bond, a carbonate bond and an alkylene group, or a single bond, preferably a linking group containing an alkylene group. It is more preferable. Among these, it is particularly preferable that R 11 and R 12 are each independently a linking group composed of an alkylene group.
  • the alkylene group preferably has 2 to 8 carbon atoms, more preferably 2 to 6 carbon atoms, and still more preferably 2 to 4 carbon atoms.
  • R 21 and R 22 each independently represents a hydrogen atom or a methyl group, and is preferably a hydrogen atom.
  • Ar 11 to Ar 14 are each independently a condensed ring group containing an aromatic ring surrounded by a broken line as one of the condensed rings, a group having L 1 as a linking group and a group having L 2 as a linking group , And R 3 to R 6 may be independently substituted with an aromatic ring surrounded by a broken line or may be substituted with a condensed ring other than the aromatic ring surrounded by a broken line.
  • MeO represents a methoxy group.
  • the compound A is preferably A-1, A-2, A-3, A-4, A-5, A-6, and A-1, A-2, A-3, A-5 A-6 is more preferable, and A-3 and A-6 are particularly preferable.
  • the content of Compound A in the curable composition is preferably 10 to 80% by mass, more preferably 20 to 70% by mass, and more preferably 30 to 60% by mass with respect to the total mass of the curable composition. More preferably, it is mass%.
  • the curable composition may contain two or more compounds A represented by the general formula (A). When 2 or more types of compounds A are contained, the total content is preferably within the above range.
  • the curable composition includes Compound B having at least one fluorine atom and at least one radical crosslinkable group in one molecule. By including such a compound, a curable composition excellent in mold transferability can be obtained.
  • the radical crosslinkable group possessed by Compound B include (meth) acryloyl group, ⁇ -fluoroacryloyl group, ⁇ -trifluoromethylacryloyl group, allyl group, vinyl group, vinyloxy group and the like.
  • a radical crosslinkable group is a (meth) acryloyl group or an allyl group.
  • Compound B may be (1) a monofunctional monomer having at least one fluorine atom and one radical crosslinkable group in one molecule, and (2) at least one fluorine atom and radical crosslinkable in one molecule. It may be a polyfunctional monomer having two or more groups, or (3) a reactive polymer having at least one fluorine atom and a radical crosslinkable group in the side chain. Further, as the compound B, two or more kinds selected from the above (1) monofunctional monomer, (2) polyfunctional monomer, and (3) reactive polymer may be used in combination.
  • Monofunctional monomers having at least one fluorine atom and one radical crosslinkable group in one molecule include, for example, 1H, 1H, 2H, 2H-heptadecafluorodecyl (meth) acrylate, 1H, 1H, 5H-octafluoropentyl (meth) acrylate, 2,2,3,3-tetrafluoropropyl (meth) acrylate, 2,2,2-trifluoroethyl (meth) acrylate, 2- (perfluorobutyl) ethyl (meth) ) Acrylate, 2- (perfluorohexyl) ethyl (meth) acrylate, and 2- (perfluorooctyl) ethyl (meth) acrylate.
  • Examples of the polyfunctional monomer having at least one fluorine atom and two or more radical crosslinkable groups in one molecule include 1,3-bis ⁇ (meth) acryloyloxy ⁇ -2,2-difluoropropane, 1,4-bis ⁇ (meth) acryloyloxy ⁇ -2,2,3,3-tetrafluorobutane, 1,5-bis ⁇ (meth) acryloyloxy ⁇ -2,2,3,3,4,4- Hexafluoropentane, 1,6-bis ⁇ (meth) acryloyloxy ⁇ -2,2,3,3,4,4,5,5-octafluorohexane, 1,7-bis ⁇ (meth) acryloyloxy ⁇ - 2,2,3,3,4,4,5,5,6,6-decafluoroheptane, 1,8-bis ⁇ (meth) acryloyloxy ⁇ -2,2,3,3,4,4,5 , 5,6,6,7,7-dodecaful Looctane,
  • Examples of the reactive polymer having at least one fluorine atom and radical crosslinkable group in the side chain include the structural unit (a) having a fluorine atom in the side chain and the structural unit having a crosslinkable group in the side chain. Mention may be made of polymers having (b).
  • the molecular weight (weight average molecular weight) of the reactive polymer having a radical crosslinkable group in the side chain is preferably 1,000 to 500,000, more preferably 3,000 to 300,000, More preferably, it is from 000 to 100,000.
  • the weight average molecular weight of the reactive polymer having a radical crosslinkable group in the side chain is a value calculated in terms of standard polystyrene by GPC (Gel Permeation Chromatography) method.
  • the structural unit (a) having a fluorine atom in the side chain a structural unit derived from a monofunctional monomer having one radical crosslinkable group in one molecule of (1) described above can be mentioned.
  • a structural unit (b) which has a crosslinkable group in a side chain the structural unit which has the following structures can be mentioned, for example.
  • R 1 and R 2 each independently represent a hydrogen atom or a methyl group.
  • a structural unit of the reactive polymer having at least one fluorine atom and a radical crosslinkable group in the side chain a structural unit other than the structural unit (a) and the structural unit (b) may be included.
  • the structural unit which has an aryl group in a side chain can be mentioned, for example.
  • the compatibility of the compound A and the compound B can be improved because the reactive polymer having a radical crosslinkable group in the side chain further has a structural unit having an aryl group in the side chain.
  • the structural unit which has the following structures can be mentioned, for example.
  • Ra represents hydrogen or a methyl group.
  • N represents an integer of 0 to 10, preferably 0 to 2, and more preferably 0 or 1.
  • Compound B has at least one fluorine atom in one molecule, and has at least one group selected from a fluoroalkyl group, a perfluoroalkyl group, a perfluoroalkylene group, and a perfluoroalkyleneoxy group. Preferably there is.
  • the proportion of fluorine atoms in one molecule of Compound B is preferably 5% by mass or more, more preferably 20% by mass or more, and further preferably 30% by mass or more.
  • the content of Compound B in the curable composition is preferably 5 to 70% by mass, more preferably 10 to 60% by mass, and more preferably 20 to 50% with respect to the total mass of the curable composition. More preferably, it is mass%.
  • the content of fluorine atoms contained in the curable composition is preferably 1% by mass or more, more preferably 5% by mass or more, and further preferably 7% by mass or more. It is particularly preferable that the content is at least mass%. Moreover, it is preferable that content of the fluorine atom contained in a curable composition is 30 mass% or less.
  • the curable composition may further contain other components in addition to Compound A and Compound B described above. Specific examples of other components include the following.
  • the curable composition further contains a (meth) acrylate monomer described later, a non-conjugated vinylidene group-containing compound, and at least one selected from a photoradical polymerization initiator and a thermal radical polymerization initiator. Also good.
  • the curable composition may contain a (meth) acrylate monomer.
  • the (meth) acrylate monomer may be a polyfunctional (meth) acrylate monomer having two or more (meth) acryloyl groups in the molecule, and may be a monofunctional (meta) having one (meth) acryloyl group in the molecule. ) May be an acrylate monomer.
  • Specific examples of the (meth) acrylate monomer include (meth) acrylate monomers described in paragraphs 0037 to 0046 of JP2012-107191A.
  • Examples of the (meth) acrylate monomer that can be preferably used in the present invention include a monofunctional (meth) acrylate monomer having an aromatic ring represented by monomer 1 (phenoxyethyl acrylate) or monomer 2 (benzyl acrylate), and monomer 3 Examples thereof include a monofunctional (meth) acrylate monomer having an aliphatic ring represented by (tricyclodecane dimethanol diacrylate) or monomer 4 (dicyclopentanyl acrylate).
  • the molecular weight of the (meth) acrylate monomer is preferably 100 to 500.
  • the method for obtaining the (meth) acrylate monomer is not particularly limited, and may be obtained commercially or may be produced by synthesis.
  • biscoat # 192 PEA (monomer 1) (manufactured by Osaka Organic Chemical Industry Co., Ltd.)
  • biscoat # 160 BZA (monomer 2) (manufactured by Osaka Organic Chemical Industry Co., Ltd.)
  • A-DCP Monomer 3) (manufactured by Shin-Nakamura Chemical Co., Ltd.)
  • FA-513AS monomer 4 (manufactured by Hitachi Chemical Co., Ltd.)
  • the content of the (meth) acrylate monomer is preferably 1 to 80% by mass with respect to the total mass of the curable composition, and is preferably 2 to 50%. More preferably, it is more preferably 3 to 40% by mass.
  • the curable composition may include a non-conjugated vinylidene group-containing compound.
  • a non-conjugated vinylidene group-containing compound compounds described in paragraphs 0016 to 0033 of JP2012-107191A can be used. This specification incorporates the contents described in paragraphs 0016 to 0033 of JP2012-107191A.
  • the molecular weight of the non-conjugated vinylidene group-containing compound is preferably 100 to 400, more preferably 120 to 350, and particularly preferably 130 to 300.
  • the method for obtaining the non-conjugated vinylidene group-containing compound is not particularly limited, and may be obtained commercially or synthesized.
  • ⁇ -caryophyllene manufactured by Inoue Fragrance Co., Ltd.
  • (+)-limonene manufactured by Tokyo Chemical Industry Co., Ltd.
  • the content of the non-conjugated vinylidene group-containing compound is preferably 0.5 to 30% by mass with respect to the total mass of the curable composition.
  • the content is more preferably 1 to 25% by mass, and further preferably 2 to 20% by mass.
  • the curable composition contains at least one selected from a thermal radical polymerization initiator and a photo radical polymerization initiator.
  • the curable composition preferably contains a thermal radical polymerization initiator.
  • cured material with high heat resistance can be shape
  • the following compounds can be used as the thermal radical polymerization initiator.
  • 1,1-di (t-hexylperoxy) cyclohexane 1,1-di (t-butylperoxy) cyclohexane, 2,2-di (4,4-di- (t-butylperoxy) cyclohexyl) propane, t-hexylperoxyisopropyl monocarbonate, t-butylperoxy-3,5,5-trimethylhexanoate, t-butylperoxylaurate, dicumyl peroxide, di-t-butylperoxide, t-butylperoxy-2 -Ethylhexanoate, t-hexylperoxy-2-ethylhexanoate, cumene hydroperoxide, t-butyl hydroperoxide, t-butylperoxy-2-ethylhexyl, 2,3-dimethyl-2,
  • a curable composition contains a hydroperoxide compound as a thermal radical polymerization initiator.
  • the hydroperoxide compound is a peroxide and a compound having a peroxy group.
  • one oxygen atom of the peroxy group (—O—O—) is substituted with a hydrogen atom, and includes a hydroperoxide group (—O—O—H).
  • a hydroperoxide compound having a hydroperoxide group in the molecule has an effect of promoting chain transfer during the polymerization of the non-conjugated vinylidene group-containing compound, and has more controllability of the three-dimensional structure when the curable composition is cured. It is possible to improve and impart deformability to the semi-cured product.
  • the method for obtaining the hydroperoxide compound is not particularly limited, and may be obtained commercially or synthesized.
  • Park Mill H-80 cumene hydroperoxide manufactured by Nippon Oil & Fats Co., Ltd. can be used.
  • the thermal radical polymerization initiator includes a hydroperoxide compound and another thermal radical polymerization initiator.
  • thermal radical polymerization initiators include non-hydroperoxide compounds.
  • the hydroperoxide compound generally has a high temperature for initiating thermal radical polymerization, it preferably contains both non-hydroperoxide compounds having a low thermal polymerization initiation temperature.
  • Non-hydroperoxide compounds include t-butyl peroxy-2-ethylhexanoate (Nippon Yushi Co., Ltd., Perbutyl O), t-butyl peroxy-2-ethylhexyl carbonate (Nippon Yushi Co., Ltd., Perbutyl E). It is preferable to use peroxyester compounds such as
  • the content of the thermal radical polymerization initiator is preferably 0.01 to 10% by mass, more preferably 0.05 to 5.0% by mass, based on the total mass of the curable composition. More preferably, it is 0.05 to 2.0% by mass.
  • a curable composition contains radical photopolymerization initiator.
  • the following compounds can be used as the radical photopolymerization initiator.
  • radical photopolymerization initiators BASF Corporation, Irgacure 184 (1-hydroxycyclohexyl phenyl ketone), Irgacure 819 (bis (2,4,6-trimethylbenzoyl) -phenylphosphine oxide), Irgacure 651 (2,2 -Dimethoxy-1,2-diphenylethane-1-one), 1- [4- (2-hydroxyethoxy) -phenyl] -2-hydroxy-2-methyl-1-propan-1-one, 2-methyl- 1- (4-methylthiophenyl) -2-morpholinopropan-1-one can be preferably used.
  • the content of the radical photopolymerization initiator is preferably 0.01 to 5.0% by mass and more preferably 0.05 to 1.0% by mass with respect to the total mass of the curable composition. Preferably, it is 0.05 to 0.5% by mass.
  • the curable composition preferably contains both a radical photopolymerization initiator and a thermal radical polymerization initiator. In this case, the total content of the radical photopolymerization initiator and the thermal radical polymerization initiator is the curable composition. It is preferably 0.01 to 10% by mass, more preferably 0.05 to 5.0% by mass, and 0.05 to 3.0% by mass with respect to the total mass of the product. Further preferred.
  • the curable composition may further include a polymer having a radical polymerizable group in the side chain, in addition to the above-described compound.
  • the polymer having a radical polymerizable group in the side chain does not contain a fluorine atom. Since the polymer having a radically polymerizable group in the side chain functions to increase the viscosity of the curable composition, it can also be called a thickener or a thickening polymer.
  • the polymer which has a radically polymerizable group in a side chain can be added when it is necessary to adjust the viscosity of a curable composition in a desired range.
  • the polymer having a radical polymerizable group in the side chain may be a homopolymer or a copolymer. Especially, it is preferable that the polymer which has a radically polymerizable group in a side chain is a copolymer.
  • the polymer having a radical polymerizable group in the side chain is a copolymer, it is sufficient that at least one copolymer component has a radical polymerizable group.
  • the polymer having a radically polymerizable group in the side chain is a copolymer, it includes a monomer unit having a radically polymerizable group in the side chain and a monomer unit having an aryl group in the side chain. More preferably, it is a copolymer.
  • radical polymerizable group examples include (meth) acrylate group, vinyl group, styryl group, allyl group and the like.
  • the polymer having a radically polymerizable group in the side chain preferably contains 5 to 100% by weight of repeating units having a radically polymerizable group, and more preferably 10 to 90% by weight. 20 to 80% by mass is more preferable.
  • the polymer having a radically polymerizable group preferably used in the side chain is listed below, but the polymer having a radically polymerizable group in the side chain is not limited to the following structure.
  • Ra and Rb each independently represent hydrogen or a methyl group.
  • a plurality of Ra in one polymer may be the same or different.
  • N represents an integer of 0 to 10, preferably an integer of 0 to 2, and more preferably 0 or 1.
  • the molecular weight (weight average molecular weight) of the polymer having a radical polymerizable group in the side chain is preferably 1,000 to 10,000,000, more preferably 5,000 to 300,000. More preferably, it is from 1,000,000 to 200,000.
  • the glass transition temperature of the polymer having a radical polymerizable group in the side chain is preferably 50 to 400 ° C., more preferably 70 to 350 ° C., and further preferably 100 to 300 ° C. .
  • the content of the polymer having a radical polymerizable group in the side chain is preferably 40% by mass or less, more preferably 30% by mass or less, and more preferably 25% by mass with respect to the total mass of the curable composition. More preferably, it is% or less. In addition, 0 mass% may be sufficient as content of the polymer which has a radically polymerizable group in a side chain, and the aspect which does not add the polymer which has a radically polymerizable group in a side chain is also preferable.
  • the curable composition may contain additives, such as a polymer other than the component mentioned above, a monomer, a dispersing agent, a plasticizer, a heat stabilizer, and a mold release agent.
  • additives such as a polymer other than the component mentioned above, a monomer, a dispersing agent, a plasticizer, a heat stabilizer, and a mold release agent.
  • cured material includes the process of photocuring the curable composition mentioned above, and / or the process of thermosetting.
  • the method for producing a cured product includes a step of forming a semi-cured product by irradiating the curable composition with light or heating the curable composition, and irradiating the obtained semi-cured product with light or semi-cured. A step of forming a cured product by heating the cured product.
  • the step of forming the semi-cured product first includes a transfer step.
  • a transfer process is a process of pressing a metal mold
  • the transfer step the other mold is pressed against the curable composition injected into one of the pair of molds to spread the curable composition.
  • cured material is what performed the chromium nitride process. Thereby, a favorable mold releasability can be obtained in a release step performed in a later step, and the manufacturing efficiency of the optical member can be increased.
  • Examples of the chromium nitride treatment include a method of forming a chromium nitride film on the mold surface.
  • a method of forming a chromium nitride film on the mold surface there are, for example, a CVD (Chemical Vapor Deposition) method and a PVD (Physical Vapor Deposition) method.
  • the CVD method is a method of forming a chromium nitride film on a substrate surface by reacting a source gas containing chromium and a source gas containing nitrogen at a high temperature.
  • the PVD method is a method of forming a chromium nitride film on the surface of a substrate using an arc discharge (arc type vacuum deposition method).
  • arc type vacuum deposition method when a cathode (evaporation source) made of, for example, chromium is disposed in a vacuum vessel, an arc discharge is caused between the cathode and the wall of the vacuum vessel via a trigger, and the cathode is evaporated.
  • ionization of the metal by arc plasma is performed, a negative voltage is applied to the substrate, and a reaction gas such as nitrogen gas is introduced into the vacuum vessel by about several tens of mTorr (1.33 Pa), thereby bringing the ionized metal and the reaction gas into the substrate
  • a reaction gas such as nitrogen gas is introduced into the vacuum vessel by about several tens of mTorr (1.33 Pa), thereby bringing the ionized metal and the reaction gas into the substrate
  • the mold can be heated while pressing the contents by combining two molds, and when a low-viscosity composition is injected into the mold, the mold clearance is reached. Cause leakage. For this reason, it is preferable that the curable composition inject
  • a polymer having the above-described radical polymerizable group in the side chain may be added to the curable composition.
  • a step of forming a semi-cured product is provided.
  • the semi-cured product can be obtained by semi-curing the curable composition injected into the mold.
  • light irradiation or heating is performed.
  • such a process can also be called a semi-hardening process.
  • a semi-cured product In the step of forming a semi-cured product, at least one of light irradiation and heating is performed on the curable composition to obtain a semi-cured product having a complex viscosity of 10 5 to 10 8 mPa ⁇ s at 25 ° C. and a frequency of 10 Hz. It is preferable to form.
  • the “semi-cured product” in the present specification is a product obtained by polymerizing a curable composition, which is not completely solid and has a certain degree of fluidity.
  • a product having an upper limit value of complex viscosity of less than 1.0 ⁇ 10 9 mPa ⁇ s at 25 ° C. and a frequency of 10 Hz can be regarded as a semi-cured product. If the polymer of the curable composition has a complex viscosity of 10 5 to 10 8 mPa ⁇ s at 25 ° C. and a frequency of 10 Hz, the polymer is a semi-cured product.
  • the “cured product” is a product obtained by curing a curable composition by polymerization, and means a product in a completely solid state.
  • the light used for light irradiation is preferably ultraviolet light or visible light, and more preferably ultraviolet light.
  • a metal halide lamp, a low-pressure mercury lamp, a high-pressure mercury lamp, an ultra-high-pressure mercury lamp, a sterilization lamp, a xenon lamp, an LED (Light Emitting Diode) light source lamp, or the like is preferably used.
  • the atmosphere at the time of light irradiation is preferably air or an inert gas substitution atmosphere, and more preferably an atmosphere substituted with nitrogen until the oxygen concentration becomes 1% or less.
  • the heating semi-curing is performed so that the complex viscosity of the semi-cured product after heating at 25 ° C. and a frequency of 10 Hz is 10 5 to 10 8 mPa ⁇ s. preferable.
  • the present invention also relates to a semi-cured product produced by the method described above.
  • a semi-cured product can be preferably used in a method for producing a cured product to be described later.
  • the preferable range of the complex viscosity of the semi-cured product is the same as the preferable range of the complex viscosity of the semi-cured product in the step of forming the semi-cured product.
  • the radical photopolymerization initiator is completely consumed and may not be contained at all, or the radical photopolymerization initiator may remain.
  • the glass transition temperature of the semi-cured product is preferably ⁇ 150 to 0 ° C., more preferably ⁇ 50 to 0 ° C., and particularly preferably ⁇ 20 to 0 ° C.
  • the step of forming a cured product includes a polymerization step in which a semi-cured product is put into a mold and subjected to pressure deformation and heated to thermally polymerize or photopolymerized by light irradiation to obtain a cured product. Is preferred. In this specification, such a process can also be called a hardening process.
  • the light irradiation conditions and heating conditions in the process of forming the cured product are the same as the conditions in the semi-curing process described above.
  • the mold used in the polymerization process is also referred to as a thermoforming mold.
  • the thermoforming mold has a configuration in which two molds can be combined and heated while pressing the contents.
  • die as a shaping
  • a thermoforming mold for example, the one described in JP-A-2009-126011 can be used.
  • the metal mold has been subjected to a chromium nitride treatment.
  • the semi-cured product placed in the mold is subjected to pressure deformation, heated and thermally polymerized to obtain a cured product.
  • the pressure deformation and the heating may be performed at the same time, the heating may be performed after the pressure deformation, or the pressure deformation may be performed after the heating. It is preferable to carry out simultaneously. Further, it is also preferable that the pressure deformation and the heating are performed at the same time and the heating is further performed at a higher temperature after the pressure is stabilized.
  • the semi-cured product is heated and cured at a temperature of 150 ° C. or higher to obtain a cured product.
  • the heating temperature is 150 ° C. or higher, preferably 160 to 270 ° C., more preferably 165 to 250 ° C., and still more preferably 170 to 230 ° C.
  • the pressure in the pressure deformation is preferably 0.098 MPa to 9.8 MPa, more preferably 0.294 MPa to 4.9 MPa, and particularly preferably 0.294 MPa to 2.94 MPa.
  • the time for the thermal polymerization is preferably 30 to 1000 seconds, more preferably 30 to 500 seconds, and particularly preferably 60 to 300 seconds.
  • the atmosphere at the time of thermal polymerization is preferably air or an inert gas substitution atmosphere, and more preferably an atmosphere substituted with nitrogen until the oxygen concentration becomes 1% or less.
  • a release step is provided after the curing step.
  • thermal polymerization is performed in the curing step, it is preferable to pull the mold away from the cured product in the temperature range of 150 to 250 ° C. in the mold release step.
  • the temperature in the mold release step within the above range, the mold can be easily separated from the cured product, and the production efficiency can be increased.
  • cured material of this invention is not restricted to this, In the range which does not deviate from this invention, it can change suitably.
  • the mold used in the transfer process and the semi-curing process may be used as it is in the curing process. After performing the semi-curing process, the mold is separated from the semi-cured product, and this semi-cured product is separated from another mold.
  • the curing step may be performed by moving to a (thermoforming mold). In this case, it is preferable that the above-described chromium treatment is performed on the mold used in the semi-curing process and the curing process.
  • the curable composition in the mold may be irradiated with light and heated. Thereby, the semi-hardened material which has a desired degree of hardening can be obtained reliably.
  • the present invention also relates to a semi-cured product of the curable composition.
  • the semi-cured product is formed by semi-curing the above-described curable composition.
  • the semi-cured product of the present invention is preferably produced by the above-described method for producing a semi-cured product.
  • the semi-cured product preferably has a complex viscosity of 10 5 to 10 8 mPa ⁇ s at 25 ° C. and a frequency of 10 Hz.
  • the present invention also relates to a cured product of the curable composition.
  • the cured product is formed by curing the semi-cured component described above. It is preferable that the hardened
  • the cured product of the present invention preferably has a maximum thickness of 0.1 to 10 mm.
  • the maximum thickness is more preferably 0.1 to 5 mm, and particularly preferably 0.15 to 3 mm.
  • the cured product of the present invention preferably has a maximum diameter of 1 to 1000 mm.
  • the maximum diameter is more preferably 2 to 200 mm, and particularly preferably 2.5 to 100 mm.
  • the present invention also relates to an optical member including the above-described cured product. Since the hardened
  • the kind of the optical member of the present invention is not particularly limited. In particular, it can be suitably used as an optical member utilizing the excellent optical characteristics of the curable composition, particularly as an optical member that transmits light (so-called passive optical member).
  • optical functional device including such an optical member
  • various display devices liquid crystal display, plasma display, etc.
  • various projector devices OHP (Overhead projector), liquid crystal projector, etc.
  • optical fiber communication devices optical waveguide, An optical amplifier etc.
  • a photographing device such as a camera and a video, etc.
  • passive optical member used for an optical functional device for example, a lens, a prism, a prism sheet, a panel (plate-shaped molded body), a film, an optical waveguide (film-like or fiber-like), an optical disk, and an LED sealing Examples thereof include agents.
  • Such passive optical members include any coating layer, if necessary, such as a protective layer that prevents mechanical damage to the coated surface due to friction and wear, and an undesirable wavelength that causes deterioration of inorganic particles and substrates.
  • Light absorption layer that absorbs light transmission shielding layer that suppresses or prevents transmission of reactive low molecules such as moisture and oxygen gas, antiglare layer, antireflection layer, low refractive index layer, etc. It may be provided.
  • the optional coating layer include a transparent conductive film and gas barrier film made of an inorganic oxide coating layer, and a gas barrier film and hard coat film made of an organic coating layer.
  • a coating method for forming the coating layer a known coating method such as a vacuum deposition method, a CVD method, a sputtering method, a dip coating method, or a spin coating method can be used.
  • the optical member using the cured product of the present invention is particularly preferably used for a lens substrate.
  • the lens substrate produced using the curable composition of the present invention has a low Abbe number, and preferably has high refractive properties, light transmittance and light weight, and is excellent in optical properties.
  • the refractive index of the lens substrate can be arbitrarily adjusted by appropriately adjusting the type of monomer constituting the curable composition.
  • the “lens substrate” means a single member that can exhibit a lens function. A film or a member can be provided on the surface or the periphery of the lens substrate according to the use environment or application of the lens.
  • a protective film, an antireflection film, a hard coat film, or the like can be formed on the surface of the lens substrate. Moreover, it can be set as the compound lens laminated
  • the lens substrate When the lens substrate is used as a lens, the lens substrate itself may be used alone as a lens, or may be used as a lens by adding the above-described film, frame, or other lens substrate.
  • the type and shape of the lens using the lens substrate are not particularly limited.
  • the lens base material is preferably used for imaging lenses such as mobile phones and digital cameras, imaging lenses such as televisions and video cameras, vehicle-mounted lenses, and endoscope lenses.
  • Compound A-6 was synthesized in the same manner as in the synthesis of Compound A-3 except that Compound 6-1B was used instead of Compound 3-1B.
  • Compound B-1 2,2,2-trifluoroethyl acrylate (manufactured by Tokyo Chemical Industry)
  • Compound B-2 2,2,3,3,3-pentafluoropropyl acrylate (manufactured by Tokyo Chemical Industry)
  • Compound B-3 1H, 1H, 5H-octafluoropentyl acrylate (Osaka Organic Chemical Co., Ltd., Biscoat 8F)
  • Compound B-4 Diacrylic acid 2,2,3,3,4,4,5,5-octafluoro-1,6-hexanediol (manufactured by Tokyo Chemical Industry)
  • Examples 1 to 21 and Comparative Examples 1 to 3 Each component was added so that it might become a composition as described in the following table
  • Non-conjugated vinylidene group-containing compound ⁇ -caryophyllene (manufactured by Inoue Fragrance Co., Ltd.) or (+)-limonene (manufactured by Tokyo Chemical Industry Co., Ltd.) was used.
  • the optical isomer need not be particularly limited.
  • thermoset ⁇ Abbe number and partial dispersion ratio>
  • the curable compositions obtained in the examples and comparative examples were poured into a transparent glass mold having a diameter of 10 mm and a thickness of 1 mm, and heated to 200 ° C. in an atmosphere having an oxygen concentration of 1% or less to prepare a thermoset.
  • the Abbe number ( ⁇ d) and partial dispersion ratio ( ⁇ g, F) of the obtained thermoset were measured using an Abbe refractometer (manufactured by Kalnew Optical Industry Co., Ltd.).
  • ⁇ d (nd ⁇ 1) / (nF ⁇ nC) ⁇ g
  • F (ng ⁇ nF) / (nF ⁇ nC)
  • nd represents a refractive index at a wavelength of 587.56 nm
  • nF represents a refractive index at a wavelength of 486.13 nm
  • nC represents a refractive index at a wavelength of 656.27 nm
  • ng represents a refractive index at a wavelength of 435.83 nm.
  • ⁇ ( ⁇ g, F) was calculated.
  • ⁇ ( ⁇ g, F) is a graph in which the Abbe number ( ⁇ d) with respect to the d-line is the horizontal axis and the partial dispersion ratio ( ⁇ g, F) is the vertical axis, glass type A (Ohara Corporation, glass type name NSL7) Is the difference between the partial dispersion ratio ( ⁇ g, F) on the standard line and the partial dispersion ratio ( ⁇ g, F) of the target object, where the straight line connecting the glass and glass type B (Ohara Corporation, glass type name PBM2) is the standard line .
  • the thermosetting material was used for these measurements, even if it is the hardening material which performed the thermosetting after ultraviolet irradiation, there is no change in an Abbe number.
  • a cured product of the curable composition and the molding mold were separated at a rate of 0.05 mm / second to produce a composite lens (step of separating the mold). .
  • the above process was repeated 100 times to produce 100 compound lenses.

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Abstract

L'invention concerne une composition durcissable à partir de laquelle peut être moulé un objet durci présentant un nombre d'Abbe donné, l'objet durci présentant un taux de dispersion partielle (θg, F) supérieur à un taux de dispersion partielle (θg, F) estimé à partir du nombre d'Abbe. La composition durcissable est excellente du point de vue de la transférabilité du moule. L'invention concerne également l'objet durci, un élément optique et une lentille. La composition durcissable comprend un composé A représenté par la formule générale (A), un composé B ayant au moins un atome de fluor et au moins un groupe à réticulation radicalaire dans la molécule, et au moins un amorceur choisi parmi les amorceurs de polymérisation thermoradicalaire et les amorceurs de polymérisation photoradicalaire.
PCT/JP2018/003179 2017-03-15 2018-01-31 Composition durcissable, objet durci, élément optique et lentille Ceased WO2018168233A1 (fr)

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JP7252315B2 (ja) 2019-03-13 2023-04-04 富士フイルム株式会社 溶媒和物及び溶媒和物の製造方法
JPWO2020184649A1 (ja) * 2019-03-13 2021-12-16 富士フイルム株式会社 溶媒和物及び溶媒和物の製造方法
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US12173101B2 (en) 2019-08-22 2024-12-24 Fujifilm Corporation Curable composition, cured substance, optical member, and lens
JPWO2021033738A1 (fr) * 2019-08-22 2021-02-25
CN114222769A (zh) * 2019-08-22 2022-03-22 富士胶片株式会社 固化性组合物、固化物、光学部件及透镜
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CN114746453B (zh) * 2019-12-24 2024-05-07 富士胶片株式会社 固化性组合物、固化物、光学部件及透镜
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