WO2016159251A1 - プラスチックレンズ、眼鏡レンズおよび眼鏡 - Google Patents
プラスチックレンズ、眼鏡レンズおよび眼鏡 Download PDFInfo
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- WO2016159251A1 WO2016159251A1 PCT/JP2016/060703 JP2016060703W WO2016159251A1 WO 2016159251 A1 WO2016159251 A1 WO 2016159251A1 JP 2016060703 W JP2016060703 W JP 2016060703W WO 2016159251 A1 WO2016159251 A1 WO 2016159251A1
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- curable compound
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- 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
- G02B1/041—Lenses
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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
- C08F20/00—Homopolymers and 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
- C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
- C08F20/10—Esters
- C08F20/26—Esters containing oxygen in addition to the carboxy oxygen
-
- 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
- C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
- C08F220/28—Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety
-
- 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
- C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
- C08F222/10—Esters
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
- C08K5/0041—Optical brightening agents, organic pigments
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- G—PHYSICS
- G02—OPTICS
- G02C—SPECTACLES; SUNGLASSES OR GOGGLES INSOFAR AS THEY HAVE THE SAME FEATURES AS SPECTACLES; CONTACT LENSES
- G02C7/00—Optical parts
- G02C7/02—Lenses; Lens systems ; Methods of designing lenses
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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
- 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
- C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
- C08F220/28—Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety
- C08F220/285—Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety and containing a polyether chain in the alcohol moiety
Definitions
- the present invention relates to a plastic lens, a spectacle lens, and spectacles provided with the spectacle lens.
- Plastics have the advantage of being lighter and harder to break than glass, so molded bodies (plastic lenses) molded from plastic into lens shapes are widely used as various lenses such as eyeglass lenses.
- a curable composition containing a curable compound also referred to as a plastic lens raw material liquid
- a curable composition containing a curable compound also referred to as a plastic lens raw material liquid
- a (meth) acrylic curable compound is widely used as described in, for example, JP-A-2013-241577.
- the (meth) acrylic curable compound is a polymerizable group selected from the group consisting of an acryloyloxy group, a methacryloyloxy group, an acryloyl group, and a methacryloyl group (hereinafter also referred to as “(meth) acrylic polymerizable group”).
- (meth) acrylic polymerizable group hereinafter also referred to as “(meth) acrylic polymerizable group”.
- the curable composition containing such a (meth) acrylic curable compound is polymerized and cured by, for example, heat treatment in a mold, and then released from the mold to cure the curable composition.
- a plastic lens can be obtained.
- a plastic lens obtained by curing a curable composition containing a (meth) acrylic curable compound is very small on the lens surface after being taken out of the mold after cast polymerization. It was found that unevenness (hereinafter also referred to as “surface damage”) may occur. Such surface damage causes deterioration in the appearance quality of the plastic lens, and if it becomes severe, it also affects the optical homogeneity.
- One embodiment of the present invention is a plastic lens obtained by curing a curable composition containing a (meth) acrylic curable compound, and provides a high-quality plastic lens in which occurrence of surface damage is suppressed.
- the surface damage may be caused by, for example, a part of the extreme surface layer portion of the cured body cured in the mold during mold release after casting polymerization. It has been found that debris generated by peeling off a part of the end portion and debris generated in the rounding process (peripheral molding process) after mold release are caused by adhering to the lens surface. More specifically, as a result of the study by the present inventor, it is the cause of the minute unevenness (surface damage) that the portion where the above-mentioned debris adheres on the lens surface is locally swollen with the passage of time. ,found.
- the plastic lens according to one embodiment of the present invention A plastic lens obtained by curing a curable composition containing a curable compound,
- the curable composition contains 50 parts by mass or more of a (meth) acrylic curable compound with respect to 100 parts by mass of the total amount of the curable compound, and
- FT-IR Fourier transform infrared spectrophotometer
- the present inventor believes that the absorbance ratio determined by the above formula 1 can be an indicator of the degree of progress of polymerization in a curable composition containing a (meth) acrylic curable compound.
- the surface damage can be reduced on the surface of the plastic lens by allowing the polymerization to proceed so that the absorbance ratio becomes 7.0% or less. It was issued.
- the present inventor is responsible for the occurrence of the above-mentioned surface damage that the fragment derived from the plastic lens itself that is not sufficiently polymerized and contains a large amount of unpolymerized components alters the surface of the plastic lens.
- the fact that the occurrence of surface damage in a plastic lens having an absorbance ratio of 7.0% or less can be suppressed is not due to a simple phenomenon in which deformation due to debris is suppressed by increasing the surface hardness due to the progress of polymerization. Suggested by the phenomenon.
- the above is inference by the present inventor and does not limit the present invention.
- the (meth) acrylic curable compound is Component A1: Polyalkylene glycol (meth) acrylic curable compound having an average addition mole number of an alkylene oxide chain selected from the group consisting of an ethylene oxide chain and a propylene oxide chain of 10 or less, including.
- the curable composition contains 20 parts by mass or more of component A1 with respect to 100 parts by mass of the total amount of the curable compound.
- the (meth) acrylic curable compound is Component A2: a polyalkylene glycol (meth) acrylic curable compound having an average addition mole number of an alkylene oxide chain selected from the group consisting of an ethylene oxide chain and a propylene oxide chain in the range of 11 to 30, including.
- the curable composition contains 5 to 50 parts by mass of component A2 with respect to 100 parts by mass of the total amount of the curable compound.
- the plastic lens is a photochromic lens containing a photochromic dye.
- a plastic lens photochromic lens
- the photochromic dye develops and fades in response to light, causing plastic lenses to develop colors in bright outdoors and exhibit the same anti-glare properties as color lenses. The property of recovering can be imparted.
- the curable composition further includes an ethylenically unsaturated double bond-containing curable compound other than the (meth) acrylic curable compound.
- the curable composition further includes a radical polymerization initiator.
- the curable composition contains 1.00 to 6.00 parts by mass of the radical polymerization initiator with respect to 100 parts by mass of the total amount of the curable compound.
- the radical polymerization initiator is an organic peroxide.
- the radical polymerization initiator is a peroxyester compound.
- the radical polymerization initiator is Component B1: A radical polymerization initiator having a 10-hour half-life temperature of 30 ° C. or more and less than 60 ° C.
- Component B 2 A radical polymerization initiator having a 10-hour half-life temperature of 60 ° C. or more and 80 ° C. or less, including.
- the curable composition contains 0.50 to 5.00 parts by mass of component B1 and 0.01 to 1.00 parts by mass of component B2 with respect to 100 parts by mass of the total amount of the curable compound. .
- a further aspect of the present invention relates to a spectacle lens including at least a lens base material, wherein the lens base material is the plastic lens described above.
- a further aspect of the present invention relates to spectacles having the spectacle lens and a frame to which the spectacle lens is attached.
- a high-quality plastic lens in which occurrence of surface damage is suppressed a spectacle lens including the plastic lens, and spectacles including the spectacle lens.
- 2 shows infrared spectra obtained for the plastic lenses of Examples 1 to 3 by FT-IR measurement.
- 2 shows infrared spectra obtained for the plastic lenses of Examples 4 to 6 by FT-IR measurement.
- 2 shows infrared spectra obtained for the plastic lenses of Comparative Examples 1 to 3 by FT-IR measurement.
- the plastic lens of the present invention is a plastic lens obtained by curing a curable composition containing a curable compound, and the curable composition contains 50 parts by mass or more of 100 parts by mass of the total amount of the curable compound (
- FT-IR Fourier transform infrared spectrophotometer
- the maximum absorbance Abs1 at a wave number of 1680 to 1620 cm ⁇ 1 is 7.0% or less.
- Absorbance ratio (%) (Abs1 / Abs2) ⁇ 100 Formula 1
- the plastic lens of the present invention is calculated by the equation 1 for the maximum absorbance Abs2 at the wave number of 1800 to 1690 cm ⁇ 1 of the maximum absorbance Abs1 at the wave number of 1680 to 1620 cm ⁇ 1 in the infrared spectrum obtained by measuring with this lens by FT-IR.
- the absorbance ratio is 7.0% or less.
- the FT-IR measurement is performed by the KBr method using a measurement sample obtained by partially cutting out a plastic lens to be measured.
- the absorbance peak at wave numbers 1680 to 1620 cm ⁇ 1 is a peak derived from an ethylenically unsaturated double bond possessed by various curable compounds including (meth) acrylic curable compounds.
- the ethylenically unsaturated double bond means a carbon-carbon double bond, and a polymerizable group possessed by various curable compositions such as a (meth) acryl polymerizable group possessed by a (meth) acrylic curable composition.
- a polymerizable group possessed by various curable compositions such as a (meth) acryl polymerizable group possessed by a (meth) acrylic curable composition.
- the intensity of the peak decreases as the number of ethylenically unsaturated double bonds subjected to polymerization reaction increases.
- the absorbance peak at a wave number of 1800 to 1690 cm ⁇ 1 is derived from a carbonyl group (— (C ⁇ O) —) contained in the (meth) acryl polymerizable group of the (meth) acrylic curable compound. It is a peak.
- the carbonyl group is not a group contributing to the polymerization reaction, the peak intensity (maximum absorbance Abs2) at a wave number of 1800 to 1690 cm ⁇ 1 takes a constant value regardless of the progress of the polymerization. Therefore, the absorbance ratio of the maximum absorbance Abs1 to the maximum absorbance Abs2 calculated by Equation 1 means that the polymerization proceeds as the value decreases. Then, by causing the polymerization of the plastic lens to proceed so that the absorbance ratio is 7.0% or less, it is possible to suppress the occurrence of the surface damage described above in the plastic lens. As a result of the diligent study of the person, it was newly discovered. The inference by the present inventor regarding this point is as described above.
- the absorbance ratio is preferably 6.0% or less, more preferably 5.0% or less, still more preferably 4.0% or less, and still more preferably 3.5%. % Or less.
- the absorbance ratio is, for example, 2.0% or more. However, the lower the ratio from the viewpoint of suppressing surface damage, the better. Therefore, the absorbance ratio may be less than 2.0%.
- the absorbance ratio can be reduced by setting the curable composition to a composition that facilitates polymerization, and can also be reduced by promoting the polymerization under polymerization conditions.
- composition of curable composition The plastic lens of the present invention is formed by curing a curable composition containing 50 parts by mass or more of a (meth) acrylic curable compound with respect to 100 parts by mass of the total amount of the curable compound.
- the said curable composition contains 50 mass parts or more of (meth) acrylic-type curable compounds with respect to 100 mass parts of curable compound whole quantity.
- the progress of polymerization of such a curable composition can be evaluated using the absorbance ratio described above as an index.
- the (meth) acrylic curable compound is preferably contained in the curable composition in an amount of 70 parts by mass or more, more preferably 80 parts by mass or more, and more preferably 90 parts by mass or more with respect to 100 parts by mass of the total amount of the curable compound. More preferably, it is more preferably 95 parts by mass or more.
- the curable composition preferably contains a curable compound other than the (meth) acrylic curable compound.
- the content of the (meth) acrylic curable compound can be, for example, 99 parts by mass or less or 98 parts by mass or less with respect to 100 parts by mass of the total amount of the curable compound.
- the plastic lens of the present invention can be a photochromic lens.
- the content of the curable compound other than the (meth) acrylic curable compound contained in the curable composition is that of the (meth) acrylic curable compound.
- the content is preferably in the range of 0.5 to 20 parts by mass and more preferably in the range of 1 to 10 parts by mass with respect to 100 parts by mass. Moreover, even when the plastic lens of this invention is not a photochromic lens, it is preferable that content of curable compounds other than the (meth) acrylic-type curable compound contained in the said curable composition is the said range.
- all the polymerizable compounds contained in the composition may be (meth) acrylic curable compounds. That is, the content of the (meth) acrylic curable compound in the curable composition may be 100 parts by mass with respect to 100 parts by mass of the total amount of the curable compound.
- the (meth) acrylic curable compound contained in the curable composition may be one kind, two or more kinds, and preferably two or more kinds.
- the above content refers to the total content thereof.
- this point is the same also about content of the other component which may be contained in the said curable composition mentioned later for details.
- the (meth) acrylic curable compound contained in the curable composition is preferably a polyfunctional compound containing two or more (meth) acrylic polymerizable groups in one molecule.
- the number of (meth) acrylic polymerizable groups contained in one molecule of the functional compound is more preferably 2 to 6, and further preferably 2 or 3.
- the (meth) acrylic curable compound is a polyfunctional compound, the (meth) acrylic polymerizable groups contained in one molecule may have the same structure or different structures.
- the curable composition is an alkylene oxide chain (hereinafter referred to as “EO / PO”) selected from the group consisting of at least an ethylene oxide chain (EO chain) and a propylene oxide chain (PO chain) as a (meth) acrylic curable compound. It is preferable to include a polyalkylene glycol (meth) acrylic curable compound having a “chain”.
- the alkylene oxide chain is Wherein R is a hydrogen atom or a methyl group, those having R as a hydrogen atom are ethylene oxide chains, and those having R as a methyl group are propylene oxide chains.
- N and m are each independently an integer of 1 or more. When n is an integer of 2 or more, n existing Rs may be the same or different. The same applies to m.
- the curable composition may contain only one type of polyalkylene glycol (meth) acrylic curable compound having an EO / PO chain, may contain two or more types having different structures, and have different structures. It is preferable that 2 or more types are included.
- the content of the polyalkylene glycol (meth) acrylic curable compound having an EO / PO chain with respect to 100 parts by mass of the total amount of the curable compound contained in the composition is preferably 25 parts by mass or more, and more preferably 40 parts. The range is from 80 parts by mass.
- content described about a certain component shall mean those total content, when two or more types from which a structure differs are contained as this component.
- the curable composition contains at least an EO / PO chain average addition mole number of 10 or less as a polyalkylene glycol (meth) acrylic curable compound.
- the average added mole number of EO / PO chain is the total number of EO / PO chains contained in one molecule of the compound.
- the average added mole number of the EO / PO chain of the compound having the partial structure represented by the above (a) as the EO / PO chain is n
- the EO of the compound having the partial structure represented by the above (b) The average added mole number of the / PO chain is m
- the average added mole number of the EO / PO chain of the compound having the partial structure represented by (a) and the partial structure represented by (b) is n + m.
- the average added mole number of the EO / PO chain of the A compound having the partial structure represented by the above (a) is A ⁇ n
- the A number of the moieties represented by the above (a) is A ⁇ m
- the average added mole number is a value determined by 1 H-NMR.
- the curable composition preferably contains a polyalkylene glycol (meth) acrylic curable compound (component A1) having an average EO / PO chain addition mole number of 10 or less from the viewpoint of further suppressing surface damage.
- the average added mole number of the EP / PO chain of the component A1 is preferably in the range of 2 to 9 from the viewpoint of further suppressing the surface damage.
- the content of component A1 in the curable composition is preferably 20 parts by mass or more with respect to 100 parts by mass of the total amount of the curable compound contained in the curable composition, from the viewpoint of further suppressing surface damage. 30 parts by mass or more, and more preferably 40 parts by mass or more. Further, from the viewpoint of increasing the mechanical strength of the plastic lens of the present invention, the content of component A1 in the curable composition is 80 masses relative to 100 mass parts of the total amount of curable compounds contained in the curable composition. Part or less, preferably 70 parts by weight or less, and more preferably 60 parts by weight or less.
- the curable composition is a polyalkylene glycol (meth) acrylic curable compound having an EO / PO chain and a compound having an average added mole number larger than that of Component A1. It is preferable to contain. The inclusion of such a compound is preferable from the viewpoint of improving the photoresponsiveness of the photochromic lens.
- a polyalkylene glycol (meth) acrylic curable compound (component A2) having an average EO / PO chain addition mole number of 11 to 30 is preferable.
- the content of component A2 is preferably 5 parts by mass or more, more preferably 10 parts by mass or more, and 20 parts by mass with respect to 100 parts by mass of the total amount of the curable compound contained in the curable composition. It is still more preferable that it is above.
- the content of component A2 in the curable composition is 100 parts by mass based on the total amount of the curable compound contained in the curable composition. 50 parts by mass or less, more preferably 40 parts by mass or less, and further preferably 30 parts by mass or less.
- (Other curable compounds) As the curable compound that can be contained in the curable composition, various (meth) acrylic curable compounds other than the realkylene glycol (meth) acrylic curable compound having the EO / PO chain can be used.
- Preferred (meth) acrylic curable compounds include (meth) acrylic-amide curable compounds having an amide group (—NH— (C ⁇ O) —) together with a (meth) acrylic polymerizable group. it can.
- the (meth) acryl-amide curable compound preferably has 2 to 6 (meth) acrylic polymerizable groups in one molecule, and preferably 2 to 6 amide groups in one molecule.
- Examples of such (meth) acryl-amide-based curable compounds include (meth) acryl-amide-based polymerizable monomers represented by the general formula (1) described in JP2013-241577A. Can do. For details, refer to paragraphs 0049 to 0120 of JP 2013-241577 A and examples of the publication.
- the content of the (meth) acryl-amide curable compound in the curable composition is in the range of 10 to 50 parts by mass with respect to 100 parts by mass of the total amount of the curable compound contained in the curable composition. Is preferable, and the range of 15 to 30 parts by mass is more preferable.
- Preferred examples of the (meth) acrylic curable compound include a compound represented by the general formula (8) described in JP2013-241577A. For details, reference can be made to paragraphs 0182 to 0187 and examples in JP 2013-241577 A. In addition, a compound represented by the general formula (9) described in JP2013-241577A can also be used. For details, refer to paragraphs 0188 to 0195 and JP-A-2013-241577 and examples of the publication. Furthermore, a well-known urethane (meth) acrylate can also be used as a (meth) acrylic curable compound.
- the curable compound other than the (meth) acrylic curable compound various known ethylenically unsaturated double bond-containing curable compounds can also be used. Specific examples include substituted or unsubstituted styrene and substituted or unsubstituted styrene prepolymers.
- the prepolymer is a polymer of substituted or unsubstituted styrene, but includes a multimer containing an ethylenically unsaturated double bond and capable of undergoing a polymerization reaction.
- the ⁇ -methylstyrene dimer described later corresponds to such a prepolymer.
- Examples of the substituent for substituting styrene include linear or branched alkyl groups having 1 to 10 carbon atoms.
- about content of curable compounds other than the (meth) acrylic-type curable compound contained in the said curable composition it is as having described previously.
- the curable compound other than the (meth) acrylic curable compound various vinyl bond-containing compounds and the like can be used.
- the said curable composition can also contain 1 or more types of the well-known additive and solvent which can be contained in the curable composition used for manufacture of a plastic lens.
- the component which can be contained in the said curable composition is not limited to the following specific examples.
- the curable composition can contain a polymerization initiator for initiating polymerization of the curable compound. Since the polymerization of the (meth) acrylic curable compound can be initiated by a radical polymerization initiator, the curable composition preferably contains a radical polymerization initiator.
- the radical polymerization initiator various radical polymerization initiators that are commercially available or can be synthesized by known methods can be used.
- the radical polymerization initiator may be a thermal radical polymerization initiator that generates radicals by heat, or may be a photo radical polymerization initiator that generates radicals by light irradiation.
- thermal polymerization is preferred in terms of the process.
- the radical polymerization initiator contained in the curable composition is preferably a thermal radical initiator.
- the radical polymerization initiator contained in the curable composition is preferably an organic peroxide.
- the organic peroxide has an —O—O— bond and can initiate radical polymerization by generating oxygen radicals by heat.
- Organic peroxides include t-butyl peroxyneodecanoate, 1,1,3,3-tetramethylbutyl-peroxy-2-ethylhexanoate, t-butyl peroxypivalate, t-butyl Peroxyisobutyrate, t-butylperoxyacetate, cumylperoxyneodecanoate, t-butylperoxyoctoate, t-butylperoxyisopropylcarbonate, cumylperoxyoctoate, t-hexylperoxyneo Peroxyester compounds such as decanoate, t-hexylperoxypivalate, t-butylperoxyneohexanoate, 1,1-bis (t
- a 10-hour half-life temperature is known as an index of reactivity of the radical polymerization initiator.
- the 10-hour half-life temperature refers to a temperature at which the amount of active oxygen in the radical polymerization initiator is reduced by half in 10 hours, and is a known value in the literature or can be measured by a known method.
- the curable composition preferably contains two or more radical polymerization initiators having different 10-hour half-life temperatures from the viewpoint of controlling the rate of the polymerization reaction, and the 10-hour half-life temperatures are 30 ° C. or more and less than 60 ° C. And a radical polymerization initiator (component B2) having a 10-hour half-life temperature of 60 ° C. or higher and 80 ° C. or lower.
- the radical polymerization initiators having different 10-hour half-life temperatures are more preferably organic peroxides, and even more preferably peroxyester compounds.
- the radical polymerization initiator content of the curable composition is preferably in the range of 1.00 to 6.00 parts by mass with respect to 100 parts by mass of the total amount of curable compounds contained in the curable composition. A range of 00 to 1.50 parts by mass is more preferable.
- the content of component B1 is 0.50 to 5.00 with respect to 100 parts by mass of the total amount of the curable compound contained in the curable composition of component B1. It is preferably in the range of parts by mass, more preferably in the range of 0.70 to 3.00 parts by mass, and the content of component B2 is preferably in the range of 0.10 to 1.00 parts by mass. The range of 0.20 to 0.60 parts by mass is more preferable.
- the plastic lens of the present invention can be a photochromic lens containing a photochromic dye (photochromic compound).
- the photochromic dye is not particularly limited as long as it exhibits photochromic performance, and any known compound that can be used for the photochromic lens can be appropriately selected and used.
- any known compound that can be used for the photochromic lens can be appropriately selected and used.
- one or a mixture of two or more photochromic compounds such as a spiropyran compound, a chromene compound, a spirooxazine compound, and a fulgide compound can be used depending on the desired coloration.
- photochromic dyes reference can be made, for example, to paragraphs 0201 to 0208 in JP2013-241577A.
- the content of the photochromic dye may be appropriately set according to the type of photochromic compound to be used, but from the viewpoint of obtaining good photochromic performance, it is included in the curable composition.
- 0.001 to 3.00 parts by mass, more preferably 0.01 to 1.00 parts by mass of a photochromic dye is added to the curable composition with respect to 100 parts by mass of the total amount of the curable compound to be produced. Is preferred.
- the curable composition may further contain various additives such as a heat stabilizer, an antioxidant, an ultraviolet absorber, a release agent, an antistatic agent, and other dyes as necessary.
- additives such as a heat stabilizer, an antioxidant, an ultraviolet absorber, a release agent, an antistatic agent, and other dyes as necessary.
- the curable composition can be prepared by mixing the various components described above simultaneously or sequentially in any order.
- the preparation method is not particularly limited, and a known method can be adopted as a preparation method of the curable composition used for manufacturing the plastic lens.
- the plastic lens of the present invention can be preferably produced by a cast polymerization method using the curable composition.
- the curable composition is injected into the cavity of a mold having two molds facing each other at a predetermined interval and a cavity formed by closing the interval.
- a polymerization reaction of the curable composition is performed to obtain a plastic lens.
- the said process can be implemented similarly to the normal casting polymerization method.
- the curable composition can be injected into the mold cavity from the injection port provided on the side surface of the mold, as is usually done in the casting polymerization method.
- the curable composition is preferably polymerized by heating, whereby the curable composition is cured (preferably radical polymerization), and a molded body in which the internal shape of the cavity is transferred can be obtained.
- the polymerization conditions are not particularly limited, and the composition of the curable composition and the type of polymerization initiator are such that the polymerization proceeds until the absorbance ratio calculated by the above-mentioned formula 1 is 7.0% or less. It can set suitably according to etc.
- a mold in which the curable composition is poured into a cavity can be heated at a heating temperature of 20 to 100 ° C.
- the heating temperature in the present invention and the present specification refers to the ambient temperature at which the mold is disposed. Further, during heating, the temperature can be increased at an arbitrary temperature increase rate, and the temperature can be decreased (cooled) at an arbitrary temperature decrease rate.
- the molded body (plastic lens) inside the cavity is released from the mold.
- the plastic lens can be released from the mold by removing the upper and lower molds forming the cavity and the sealing members such as gaskets in an arbitrary order.
- a part of the extreme surface layer part or a part of the end part of the cured body generated here may be caused by peeling or a piece generated during the rounding process, which may cause surface damage.
- the absorbance ratio calculated by Equation 1 is 7.0% or less, occurrence of such surface damage can be suppressed.
- the plastic lens released from the mold can be preferably used as a lens base material for spectacle lenses.
- Plastic lenses that are used as lens base materials for spectacle lenses are usually annealed, grinding processes such as rounding processes, polishing processes, primer coat layers for improving impact resistance, and hardware for increasing surface hardness after mold release. It can attach
- various functional layers such as an antireflection layer and a water repellent layer can be formed on the plastic lens. For these, any known technique can be applied without any limitation.
- plastic lens of this invention is not limited to what is manufactured by the casting polymerization method.
- Plastic lenses manufactured by methods other than the casting polymerization method may generate fragments due to processing such as a rounding process, and the occurrence of surface damage due to adhesion of such fragments is suppressed with the plastic lens of the present invention. can do.
- the spectacle lens of the present invention is a spectacle lens including at least a lens base material, and the lens base material is a spectacle lens that is the plastic lens of the present invention described above.
- the spectacles of the present invention are spectacles having the spectacle lens of the present invention and a frame to which the spectacle lens is attached.
- the spectacle lens is as described in detail above. There is no restriction
- Examples 1 to 6, Comparative Examples 1 to 3 The various components shown in Table 1 below were mixed and dissolved, and then the dissolved air was removed by vacuum defoaming to prepare a curable composition.
- the prepared curable composition was poured into a mold cavity composed of two glass molds and a plastic gasket and polymerized by heating (heating) from 30 ° C. to 95 ° C. over 24 hours. . After polymerization, the mold is released from the mold, the rounding process (peripheral molding process) is performed, and then placed in an environment at an ambient temperature of 100 ° C. for 1 hour or longer to remove strain inside the lens generated during polymerization (annealing). The meniscus-shaped plastic lens (photochromic lens) was obtained.
- the several plastic lens was produced.
- NK ester 3PG Polyethylene glycol diacrylate (9GA): NK ester A-400 manufactured by Shin-Nakamura Chemical Co., Ltd.
- ⁇ (Meth) acrylic-amide monomer AM-01
- TMPT Trimethylolpropane trimethacrylate
- GMA Glycidyl methacrylate
- Light Ester G ⁇ ⁇ -Methylstyrene ⁇ MS
- MSD 2,4-Diphenyl-4-methyl-1-pentene manufactured by Tokyo Chemical Industry Co., Ltd.
- the transmitted light irradiated with the high-pressure mercury lamp was transmitted through a plastic lens and imaged on a white screen to confirm the occurrence of surface defects, that is, the occurrence of surface damage.
- Table 2 shows the elapsed time from the start of storage to the occurrence of surface damage. In Table 2, when no surface defects (surface damage) were observed even after 72 hours of storage, “72 hours ⁇ ” was indicated.
- the plastic lens of the example whose absorbance ratio calculated by the above-mentioned formula 1 is 7.0% or less is more damaged than the plastic lens of the comparative example whose absorbance ratio exceeds 7.0%. It can be confirmed that the occurrence of is suppressed. When the surface of the plastic lens in which the occurrence of surface damage was confirmed was visually observed, a local bulge was observed in the portion where the fragments were placed.
- One embodiment of the present invention is useful in the field of manufacturing eyeglass lenses and eyeglasses.
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Abstract
Description
しかるに、本発明者の検討によれば、(メタ)アクリル系硬化性化合物を含む硬化性組成物を硬化させてなるプラスチックレンズは、注型重合後に成形型から取り出した後に、レンズ表面に微小な凹凸(以下、「表面ダメージ」とも記載する。)が発生する場合があることが明らかとなった。このような表面ダメージは、プラスチックレンズの外観品質を低下させる原因となり、重度になると光学的均質性にも影響を及ぼすため、低減することが望まれる。
そこで本発明者は、上記知見に基づき更に鋭意検討を重ねた結果、本発明の一態様にかかるプラスチックレンズ:
硬化性化合物を含む硬化性組成物を硬化させてなるプラスチックレンズであって、
上記硬化性組成物は、硬化性化合物全量100質量部に対して50質量部以上の(メタ)アクリル系硬化性化合物を含み、かつ、
上記プラスチックレンズにおいてフーリエ変換赤外分光光度計(以下、「FT-IR」とも記載する。)により測定して得られる赤外スペクトルにおいて、波数1680~1620cm-1における最大吸光度Abs1の波数1800~1690cm-1における最大吸光度Abs2に対する下記式1:
吸光度比(%)=(Abs1/Abs2)×100 …式1
により算出される吸光度比が7.0%以下であるプラスチックレンズ、
を新たに見出した。即ち、本発明者は、上記プラスチックレンズは、前述のような破片が付着したとしても、レンズ表面に微小な凹凸(表面ダメージ)が発生し難いことを新たに見出し、本発明の一態様を完成させた。
ただし以上は本発明者による推察であって、本発明を何ら限定するものではない。
成分A1:エチレンオキサイド鎖およびプロピレンオキサイド鎖からなる群から選ばれるアルキレンオキサイド鎖の平均付加モル数が10以下であるポリアルキレングリコール(メタ)アクリル系硬化性化合物、
を含む。
成分A2:エチレンオキサイド鎖およびプロピレンオキサイド鎖からなる群から選ばれるアルキレンオキサイド鎖の平均付加モル数が11~30の範囲であるポリアルキレングリコール(メタ)アクリル系硬化性化合物、
を含む。
成分B1:10時間半減期温度が30℃以上60℃未満であるラジカル重合開始剤、および
成分B2:10時間半減期温度が60℃以上80℃以下であるラジカル重合開始剤、
を含む。
本発明のプラスチックレンズは、硬化性化合物を含む硬化性組成物を硬化させてなるプラスチックレンズであって、上記硬化性組成物は、硬化性化合物全量100質量部に対して50質量部以上の(メタ)アクリル系硬化性化合物を含み、かつ、上記プラスチックレンズにおいてフーリエ変換赤外分光光度計(FT-IR)により測定して得られる赤外スペクトルにおいて、波数1680~1620cm-1における最大吸光度Abs1の波数1800~1690cm-1における最大吸光度Abs2に対する下記式1で算出される吸光度比が7.0%以下であるプラスチックレンズである。
吸光度比(%)=(Abs1/Abs2)×100 …式1
本発明のプラスチックレンズは、このレンズにおいてFT-IRにより測定して得られる赤外スペクトルにおいて、波数1680~1620cm-1における最大吸光度Abs1の波数1800~1690cm-1における最大吸光度Abs2に対する式1により算出される吸光度比が、7.0%以下である。上記FT-IR測定は、測定対象のプラスチックレンズを一部切り出し得た測定試料を用いてKBr法により行うものとする。上記の波数1680~1620cm-1における吸光度のピークは、(メタ)アクリル系硬化性化合物をはじめとする各種硬化性化合物が有するエチレン性不飽和二重結合に由来するピークである。なおエチレン性不飽和二重結合とは、炭素-炭素二重結合をいい、(メタ)アクリル系硬化性組成物が有する(メタ)アクリル重合性基等の各種硬化性組成物が有する重合性基に含まれる。かかるピークの強度(最大吸光度Abs1)は、重合反応したエチレン性不飽和二重結合が増えるほど低下する。これに対し、波数1800~1690cm-1における吸光度のピークは、(メタ)アクリル系硬化性化合物が有する(メタ)アクリル重合性基に含まれるカルボニル基(-(C=O)-)に由来するピークである。カルボニル基は重合反応に寄与する基ではないため、波数1800~1690cm-1におけるピーク強度(最大吸光度Abs2)は、重合の進行にかかわらず一定の値を取る。したがって、式1により算出される最大吸光度Abs2に対する最大吸光度Abs1の吸光度比は、この値が小さくなるほど重合が進行していることを意味する。そして、プラスチックレンズの重合を、この吸光度比が7.0%以下となるほど進行させることにより、プラスチックレンズにおいて先に説明した表面ダメージが発生することを抑制することが可能になることが、本発明者の鋭意検討の結果、新たに見出されたものである。この点に関する本発明者による推察は、先に記載した通りである。本発明のプラスチックレンズにおいて、上記吸光度比は、好ましくは6.0%以下であり、より好ましくは5.0%以下であり、更に好ましくは4.0%以下であり、いっそう好ましくは3.5%以下である。上記吸光度比は、例えば2.0%以上であるが、表面ダメージを抑制する観点からは低いほど好ましいため、2.0%未満であってもよい。上記吸光度比は、硬化性組成物を重合を進行しやすい組成とすることによって低減することができ、重合条件により重合を促進することによっても低減することができる。
(硬化性組成物の組成)
本発明のプラスチックレンズは、硬化性化合物全量100質量部に対して50質量部以上の(メタ)アクリル系硬化性化合物を含む硬化性組成物を硬化させてなる。上記硬化性組成物は、(メタ)アクリル系硬化性化合物を硬化性化合物全量100質量部に対して50質量部以上含む。このような硬化性組成物の重合の進行は、先に記載した吸光度比を指標として評価することができる。(メタ)アクリル系硬化性化合物は、上記硬化性組成物に硬化性化合物全量100質量部に対して70質量部以上含まれることが好ましく、80質量部以上含まれることがより好ましく、90質量以上含まれることがさらに好ましく、95質量部以上含まれることが特に好ましい。
ところで、先に記載したように、本発明のプラスチックレンズは、一態様では、フォトクロミックレンズであることができる。フォトクロミックレンズの場合、光に対する応答性を向上する観点から、上記硬化性組成物に含まれる(メタ)アクリル系硬化性化合物以外の硬化性化合物の含有量は、(メタ)アクリル系硬化性化合物の含有量100質量部に対して0.5~20質量部の範囲であることが好ましく、1~10質量部の範囲であることがより好ましい。また、本発明のプラスチックレンズがフォトクロミックレンズではない場合にも、上記硬化性組成物に含まれる(メタ)アクリル系硬化性化合物以外の硬化性化合物の含有量が上記範囲であることは好ましい。
上記硬化性組成物は、(メタ)アクリル系硬化性化合物として、少なくとも、エチレンオキサイド鎖(EO鎖)およびプロピレンオキサイド鎖(PO鎖)からなる群から選ばれるアルキレンオキサイド鎖(以下、「EO/PO鎖」と記載する。)を有するポリアルキレングリコール(メタ)アクリル系硬化性化合物を含むことが好ましい。ここで上記アルキレンオキサイド鎖とは、
上記硬化性組成物に含まれ得る硬化性化合物としては、上記EO/PO鎖を有するリアルキレングリコール(メタ)アクリル系硬化性化合物以外の各種(メタ)アクリル系硬化性化合物を用いることもできる。
上記硬化性組成物は、以上説明した硬化性化合物に加えて、プラスチックレンズの製造に用いられる硬化性組成物に含まれ得る公知の添加剤や溶媒の一種以上を含むこともできる。以下、それら成分の具体例を記載するが、上記硬化性組成物に含まれ得る成分は、以下の具体例に限定されるものではない。
上記硬化性組成物は、硬化性化合物の重合を開始するための重合開始剤を含むことができる。(メタ)アクリル系硬化性化合物の重合は、ラジカル重合開始剤により開始することができるため、上記硬化性組成物は、ラジカル重合開始剤を含むことが好ましい。
先に記載したように、本発明のプラスチックレンズは、一態様では、フォトクロミック色素(フォトクロミック化合物)を含むフォトクロミックレンズであることができる。フォトクロミック色素としては、フォトクロミック性能を発揮するものであれば特に制限はなく、フォトクロミックレンズに使用し得る公知の化合物の中から、任意のものを適宜選択して用いることができる。例えばスピロピラン系化合物、クロメン系化合物、スピロオキサジン系化合物およびフルギド系化合物などのフォトクロミック化合物の中から所望の着色に応じて一種または二種以上を混合して用いることができる。フォトクロミック色素については、例えば、特開2013-241577号公報段落0201~0208を参照できる。なおフォトクロミック化合物は近年種々のものが市販されており、市販の化合物の場合、分子構造が明らかにされないことも多いが、本発明ではそれらを用いることもできる。上記硬化性組成物がフォトクロミック色素を含む場合、フォトクロミック色素の含有量は、用いるフォトクロミック化合物の種類に応じて適宜設定すればよいが、良好なフォトクロミック性能を得る観点からは、硬化性組成物に含まれる硬化性化合物全量100質量部に対して、好ましくは0.001~3.00質量部、より好ましくは0.01~1.00質量部のフォトクロミック色素を、上記硬化性組成物に添加することが好ましい。
上記硬化性組成物には、更に必要に応じ、各種添加剤、例えば熱安定剤、酸化防止剤、紫外線吸収剤、離型剤、帯電防止剤、その他染料などを含有させることができる。
上記硬化性組成物は、以上説明した各種成分を同時に、または任意の順序で順次、混合して調製することができる。調製方法は特に限定されるものではなく、プラスチックレンズの製造に用いる硬化性組成物の調製方法として公知の方法を採用することができる。
本発明のプラスチックレンズは、好ましくは、上記硬化性組成物を用いて注型重合法により製造することができる。注型重合法では、所定の間隔をもって対向する2つのモールドと、上記間隔を閉塞することにより形成されたキャビティを有する成形型の、上記キャビティへ上記硬化性組成物を注入し、上記キャビティ内で上記硬化性組成物の重合反応を行いプラスチックレンズを得る。上記工程は、通常の注型重合法と同様に実施することができる。使用する成形型の詳細については、特開2009-262480号公報(その全記載は、ここに特に開示として援用される)の段落0012~0014および同公報の図1を参照できる。
本発明の眼鏡レンズは、レンズ基材を少なくとも含む眼鏡レンズであって、レンズ基材が、上記の本発明のプラスチックレンズである眼鏡レンズである。
本発明の眼鏡は、本発明の眼鏡レンズと、この眼鏡レンズを取り付けたフレームと、を有する眼鏡である。
下記表1に示す各種成分を混合、溶解した後、真空脱泡にて溶存している空気を除去して硬化性組成物を調製した。
調製した硬化性組成物を2枚のガラスモールドとプラスチック製のガスケットからなる成型型のキャビティに注入し、加熱温度30℃から95℃まで24時間かけて加熱(昇温)して重合を行った。
重合後、成形型から離型し、丸め工程(外周成形工程)を行った後、雰囲気温度100℃の環境下に1時間以上置くことで、重合中に生じたレンズ内部のひずみ除去(アニール)を行い、メニスカス形状のプラスチックレンズ(フォトクロミックレンズ)を得た。
なお各実施例、比較例について、以下に記載する評価を行うために複数枚のプラスチックレンズを作製した。
・トリプロピレングリコールジメタクリレート(3PG):新中村化学工業社製NKエステル3PG
・ポリエチレングリコールジアクリレート(9GA):新中村化学工業社製NKエステルA-400
・ポリエチレングリコールジアクリレート(14GA):新中村化学工業社製NKエステルA-600
・2,2-ビス[4-メタクリロイルオキシポリエトキシフェニル]プロパン (BPE900):新中村化学工業社製NKエステルBPE-900
・(メタ)アクリル-アミド系モノマー(AM-01):
・グリシジルメタクリレート (GMA):共栄社化学社製ライトエステルG
・αメチルスチレン (αMS):東京化成工業社製α-Methylstyrene
・αメチルスチレンダイマー (MSD):東京化成工業社製2,4-Diphenyl-4-methyl-1-pentene
・ポリエチレングリコールアリルエーテル:日油社製ユニオックスPKA-5003
・t-ブチルパーオキシネオデカネート:日油社製パーブチルND(10時間半減期温度46.4℃)
・1,1,3,3-テトラメチルブチルパーオキシ-2-エチルヘキサネート:日油社製 パーオクタO(10時間半減期温度65.3℃)
・フォトクロミック化合物PC1:
実施例、比較例の各プラスチックレンズから測定用サンプル(サンプル片)を切り出し、Perkin Elmer製FT-IR Spectrometer装置「Spectrum One」にてKBr法を用いてFT-IR測定を行い、赤外スペクトルを得た。実施例1~3のプラスチックレンズについて得られた赤外スペクトルを図1に、実施例4~6のプラスチックレンズについて得られた赤外スペクトルを図2に、比較例1~3のプラスチックレンズについて得られた赤外スペクトルを図3に示す。
得られた赤外スペクトルにおいて、波数1680~1620cm-1における最大吸光度Abs1および波数1800~1690cm-1における最大吸光度Abs2を読み取り、前述の式1により吸光度比を算出した。
実施例、比較例の各プラスチックレンズの凸面上に、そのレンズ自体に由来する離型またはレンズの丸め工程(外周成成形型加工)で生じた破片を乗せ、破片を乗せた箇所が分かるようにレンズ表面に印を付け室温保管した。一定時間経過ごとに、レンズ表面に乗せた破片をアセトンを付けたクリーニングペーパーで拭くことで取り去り、アニール処理を行った後、破片を乗せた箇所を投影検査にて観察した。
先に記載した微小な凹凸(表面ダメージ)は、投影検査において表面欠陥として観察される。そこで、高圧水銀灯で照射した透過光をプラスチックレンズに透過させて白色スクリーンに結像させて、表面欠陥の発生、即ち表面ダメージの発生の有無を確認した。保管開始から表面ダメージが発生するまでの経過時間を、表2に示す。表2中、保管から72時間後の観察でも表面欠陥(表面ダメージ)が観察されなかった場合には、「72時間<」と表記した。
キセノンランプ(300W)光源装置を用いて、温度23℃、積算光量計で測定した紫外線強度1.2mW/cm2の条件で実施例、比較例の各プラスチックレンズ(フォトクロミックレンズを5分間発色させた後、光線照射を止めてからレンズの極大吸収波長(λmax)における吸光度が1/2まで低下するのに要する時間を、退色半減期(F1/2)と定義する。この時間が短いほど退色速度が速い、即ち光応答性に優れることになる。
・光源:ウシオ電気(株)製キセノンランプ(300W)装置「UIT-501C」
・積算光量計:ウシオ電気(株)製積算光量計「UIT-102(受光器UVD365PD)」
・瞬間マルチ測光システム:大塚電子(株)製「MCPD-3000」
Claims (15)
- 硬化性化合物を含む硬化性組成物を硬化させてなるプラスチックレンズであって、
前記硬化性組成物は、硬化性化合物全量100質量部に対して50質量部以上の(メタ)アクリル系硬化性化合物を含み、かつ、
前記プラスチックレンズにおいてフーリエ変換赤外分光光度計により測定して得られる赤外スペクトルにおいて、波数1680~1620cm-1における最大吸光度Abs1の波数1800~1690cm-1における最大吸光度Abs2に対する下記式1:
吸光度比(%)=(Abs1/Abs2)×100
により算出される吸光度比が7.0%以下であるプラスチックレンズ。 - 前記(メタ)アクリル系硬化性化合物は、
成分A1:エチレンオキサイド鎖およびプロピレンオキサイド鎖からなる群から選ばれるアルキレンオキサイド鎖の平均付加モル数が10以下であるポリアルキレングリコール(メタ)アクリル系硬化性化合物、
を含む請求項1に記載のプラスチックレンズ。 - 前記硬化性組成物は、硬化性化合物全量100質量部に対して成分A1を20質量部以上含む請求項2に記載のプラスチックレンズ。
- 前記(メタ)アクリル系硬化性化合物は、
成分A2:エチレンオキサイド鎖およびプロピレンオキサイド鎖からなる群から選ばれるアルキレンオキサイド鎖の平均付加モル数が11~30の範囲であるポリアルキレングリコール(メタ)アクリル系硬化性化合物、
を含む請求項2または3に記載のプラスチックレンズ。 - 前記硬化性組成物は、硬化性化合物全量100質量部に対して成分A2を5~50質量部含む請求項4に記載のプラスチックレンズ。
- フォトクロミック色素を含むフォトクロミックレンズである請求項1~5のいずれか1項に記載のプラスチックレンズ。
- 前記硬化性組成物は、(メタ)アクリル系硬化性化合物以外のエチレン性不飽和二重結合含有硬化性化合物を更に含む請求項1~6のいずれか1項に記載のプラスチックレンズ。
- 前記硬化性組成物は、ラジカル重合開始剤を更に含む請求項1~7のいずれか1項に記載のプラスチックレンズ。
- 前記硬化性組成物は、硬化性化合物全量100質量部に対して前記ラジカル重合開始剤を1.00~6.00質量部含む請求項8に記載のプラスチックレンズ。
- 前記ラジカル重合開始剤は、有機過酸化物である請求項8または9に記載のプラスチックレンズ。
- 前記ラジカル重合開始剤は、パーオキシエステル化合物である請求項10に記載のプラスチックレンズ。
- 前記ラジカル重合開始剤は、
成分B1:10時間半減期温度が30℃以上60℃未満であるラジカル重合開始剤、および
成分B2:10時間半減期温度が60℃以上80℃以下であるラジカル重合開始剤、
を含む請求項8~11のいずれか1項に記載のプラスチックレンズ。 - 前記硬化性組成物は、硬化性化合物全量100質量部に対して、成分B1を0.50~5.00質量部含み、かつ成分B2を0.01~1.00質量部含む請求項12に記載のプラスチックレンズ。
- レンズ基材を少なくとも含む眼鏡レンズであって、
前記レンズ基材が、請求項1~13のいずれか1項に記載のプラスチックレンズである眼鏡レンズ。 - 請求項14に記載の眼鏡レンズと、該眼鏡レンズを取り付けたフレームと、を有する眼鏡。
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AU2016240876A AU2016240876B2 (en) | 2015-03-31 | 2016-03-31 | Plastic lens, spectacle lens, and spectacles |
JP2017510197A JP6400184B2 (ja) | 2015-03-31 | 2016-03-31 | プラスチックレンズ、眼鏡レンズおよび眼鏡 |
CN201680017458.5A CN107430209B (zh) | 2015-03-31 | 2016-03-31 | 塑料镜片、眼镜镜片及眼镜 |
EP16773131.4A EP3279705B1 (en) | 2015-03-31 | 2016-03-31 | Plastic lens, eyeglass lens, and eyeglasses |
US15/718,283 US11187828B2 (en) | 2015-03-31 | 2017-09-28 | Plastic lens, spectacle lens, and spectacles |
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EP3279705B1 (en) | 2019-11-13 |
CN107430209B (zh) | 2020-11-17 |
EP3279705A4 (en) | 2018-11-07 |
JPWO2016159251A1 (ja) | 2018-02-15 |
US20180017711A1 (en) | 2018-01-18 |
EP3279705A1 (en) | 2018-02-07 |
AU2016240876A1 (en) | 2017-10-26 |
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