Photochromic lens manufacturing method, photochromic lens

Abstract

This production method for a photochromic lens uses an injection molding device (10) that comprises a substrate (12) that is an approximate circle, a resin substrate (14) that is an approximate circle and is arranged opposite a surface (12a) of the substrate (12), a fixing member (16) that fixes a circumferential end part of the substrate (12) and a circumferential end part of the resin substrate (14), a gap (20) that is formed between the substrate (12) and the resin substrate (14) and has a width of 0.1–2.5 mm in the thickness direction at an approximate circle center part, an injection part (18) that is provided to the fixing member (16) and is for injecting a polymerizable composition into the gap (20), and a space (22) that is formed at at least a portion of the circumferential edge of the gap (20) and allows the injection part (18) to communicate with the gap (20), the space (20) being formed between the substrate (12) and a notch part (24) that is formed in at least a portion of the circumferential edge of the resin substrate (14), and the width i of the space (22) in the thickness direction being greater than the width of the gap (20) in the thickness direction. The production method includes a step for injecting the polymerizable composition through the injection part (18) to fill the polymerizable composition into the gap (20) via the space (22), a step for heating the filled polymerizable composition to polymerize and harden the polymerizable composition and form a photochromic layer on the resin substrate (14), and a step for removing the resulting laminate of the resin substrate (14) and the photochromic layer. The polymerizable composition includes an isocyanate compound, a thiol compound, a polyol compound, and a photochromic compound.

Description

[Technical Field]

[0001] The present invention relates to a method for manufacturing a photochromic lens, and to a photochromic lens. [Background technology]

[0002] Examples of methods for polymerizing a composition containing a polymerizable compound to obtain a molded article include cast polymerization. In cast polymerization, an injection molding device is generally used, which includes two mold substrates facing each other, the peripheral edges of which are fixed with a fixing member, and a means for injecting the composition into the space between the two mold substrates. The composition is then injected into the space and subsequently polymerized and cured to obtain a molded article.

[0003] In recent years, the development of plastic lenses with photochromic properties has been progressing. There are several methods for producing plastic lenses with photochromic properties. Examples of methods for producing plastic lenses include the in-mass method (Patent Document 1), in which a photochromic compound is added to a plastic lens substrate to produce a photochromic lens, and the coating method (Patent Document 2), in which a plastic lens substrate to which no photochromic compound has been added is coated with a coating containing a photochromic compound to produce a photochromic lens. Furthermore, Patent Document 3 discloses a method for producing a molded body using a predetermined mold. [Prior art documents] [Patent documents]

[0004] [Patent Document 1] International Publication No. 2012 / 141306 [Patent Document 2] International Publication No. 2003 / 58300 [Patent Document 3] International Publication No. 2020 / 230889 [Non-patent literature]

[0005] [Non-Patent Document 1] P. Alexandridis, TA Hatton / Colloids Surfaces A: Physicochem. Eng. Aspects 96 (1995) 1-46 [Non-patent document 2] Phys. Chem. Chem. Phys., 1999, 1, 3331-3334 Summary of the Invention [Problem to be solved by the invention]

[0006] In order for a photochromic lens to exhibit its effect, a predetermined amount of photochromic compound must be present on the objective surface side that receives light. In the photochromic lenses obtained by the in-mass method described in Patent Document 1, a composition based on the concentration of the photochromic compound required on the objective surface side is used, so the total amount of photochromic compound in the entire lens is large, and initial coloring may be observed in some cases.

[0007] Photochromic lenses obtained by the coating method described in Patent Document 2 require a thin coating layer formed on the objective surface side to contain a predetermined amount of photochromic compound at a high concentration, and initial coloring may be observed in some cases. Patent Document 3 does not specifically disclose a method for manufacturing a photochromic lens, nor does it suggest any problems that may arise when a photochromic compound is used. [Means for solving the problem]

[0008] As a result of extensive research, the inventors have found that a specific manufacturing method can be used to form a photochromic lens with a two-layer structure, with the layer on the objective surface side containing the photochromic compound having a specific thickness, thereby allowing the photochromic compound to be contained in an appropriate concentration only in the layer on the objective surface side, and the resulting photochromic lens has reduced initial coloring and excellent photochromic response, thereby completing the present invention. That is, the present invention can be shown as follows.

[0009] [1] A substantially circular substrate; a substantially circular resin substrate disposed opposite the surface of the substrate; a fixing member for fixing a peripheral edge of the substrate and a peripheral edge of the resin substrate; A gap having a width of 0.1 to 2.5 mm in the thickness direction at the center of the approximately circle formed between the substrate and the resin substrate; an injection portion provided in the fixing member for injecting a polymerizable composition into the gap; a space formed on at least a portion of the periphery of the gap, the space communicating with the injection portion and the gap; a method for manufacturing a photochromic lens using an injection molding apparatus, wherein the space is formed in at least a part of a periphery of the resin substrate, and a width of the space in a thickness direction is larger than a width of the gap in the thickness direction, injecting the polymerizable composition from the injection portion and filling the gap with the polymerizable composition through the space; a step of heating the filled polymerizable composition to polymerize and harden it, thereby forming a photochromic layer on the resin substrate; removing the obtained laminate composed of the resin substrate and the photochromic layer; Including, The method for producing a photochromic lens, wherein the polymerizable composition contains an isocyanate compound, a thiol compound, a polyol compound, and a photochromic compound. [2] The method for producing a photochromic lens according to [1], wherein the polymer composition contains the photochromic compound in an amount of 100 to 10,000 ppm. [3] The method for producing a photochromic lens according to [1] or [2], wherein the photochromic compound is a naphthopyran-based compound. [4] The method for producing a photochromic lens according to any one of [1] to [3], wherein the polyol compound is a compound represented by the following general formula (iia): [ka] (In general formula (iia), R1 and R2 represent a hydrogen atom or an alkyl group having 1 to 18 carbon atoms, and at least one of them is a hydrogen atom. Multiple R1s may be the same or different, and multiple R2s may be the same or different. m represents an integer of 15 to 500.) [5] The method for producing a photochromic lens according to any one of [1] to [4], wherein the resin substrate contains a thiourethane resin. [6] The method for producing a photochromic lens according to any one of [1] to [5], wherein the viscosity (25° C.) of the polymerizable composition is 5 to 1000 mPa·s. [7] After the step of removing the laminate, A method for manufacturing a photochromic lens according to any one of [1] to [6], comprising a step of removing the polymerizable composition that has been polymerized and cured in the space around the periphery of the laminate, and exposing the photochromic layer obtained by polymerization and curing in the gap at the end face of the laminate. [8] A photochromic layer having an objective surface and a resin substrate laminated on the photochromic layer, the thickness of the approximately circular center of the photochromic layer is 0.1 to 2.5 mm; A photochromic lens in which the photochromic layer contains a photochromic compound. [9] The photochromic lens according to [8], wherein the photochromic layer has a four-point average thickness at the periphery of the lens of 0.1 to 2.5 mm.

[10] The photochromic lens according to [8] or [9], wherein the difference between the four-point average thickness of the peripheral edge of the photochromic layer and the thickness of the approximately circular center of the photochromic layer is 0.3 mm or less.

[11] The photochromic lens according to [8] or [9], wherein the thickness of at least a portion of the periphery of the photochromic layer is thicker than the thickness of the portion surrounded by the periphery.

[12] The photochromic lens according to any one of [8] to

[11] , wherein the photochromic layer contains the photochromic compound in an amount of 100 to 10,000 ppm.

[13] The photochromic lens according to any one of [8] to

[12] , wherein the photochromic lens has an initial luminous transmittance of 80% or more.

[14] The photochromic lens according to any one of [8] to

[13] , wherein the photochromic layer having the objective surface is in contact with the resin substrate.

[15] The photochromic lens according to any one of [8] to

[14] , wherein the photochromic compound is a naphthopyran-based compound.

[16] The photochromic lens according to any one of [8] to

[15] , wherein the photochromic layer further contains an isocyanate compound, a thiol compound, and a polyol compound.

[17] The photochromic lens according to

[16] , wherein the polyol compound is a compound represented by the following general formula (iia): [ka] (In general formula (iia), R1 and R2 represent a hydrogen atom or an alkyl group having 1 to 18 carbon atoms, and at least one of them is a hydrogen atom. Multiple R1s may be the same or different, and multiple R2s may be the same or different. m represents an integer of 15 to 500.)

[18] The photochromic lens according to any one of [8] to

[17] , wherein the resin substrate contains a polythiourethane resin.

[0010] In the present invention, the term "initial" means a state in which the photochromic compound is not irradiated with light and has not yet developed color. [Effects of the Invention]

[0011] According to the present invention, it is possible to provide a method for producing a photochromic lens that can produce a photochromic lens in which initial coloring is suppressed and which also has excellent photochromic response. [Brief explanation of the drawings]

[0012] [Figure 1] FIG. 1 is a schematic cross-sectional view showing a casting molding apparatus according to a first embodiment. [Figure 2] FIG. 2 is a schematic plan view showing the injection molding apparatus of the first embodiment. [Figure 3] FIG. 3 is an enlarged cross-sectional view schematically showing another aspect of the spatial cross section in the injection molding apparatus of the first embodiment. [Figure 4] FIG. 4 is an enlarged cross-sectional view schematically showing another aspect of the spatial cross section in the injection molding apparatus of the first embodiment. [Figure 5] FIG. 5 is an enlarged cross-sectional view schematically showing another aspect of the spatial cross section in the injection molding apparatus of the first embodiment. [Figure 6] FIG. 6 is a schematic cross-sectional view showing a casting molding apparatus according to the second embodiment. [Figure 7] FIG. 7 is a schematic cross-sectional view of the laminated lens (laminate) of this embodiment. DETAILED DESCRIPTION OF THE INVENTION

[0013] The method for producing the photochromic lens of the present invention will now be described. The method for producing a photochromic lens of the present invention includes the steps of: The molding is performed using an injection molding device comprising: a substantially circular substrate; a substantially circular resin substrate arranged opposite the surface of the substrate; a fixing member for fixing the peripheral edges of the substrate and the resin substrate; a gap formed between the substrate and the resin substrate and having a width in the thickness direction of 0.1 to 2.5 mm at the approximately circular center; an injection part provided in the fixing member for injecting a polymerizable composition into the gap; and a space formed on at least a part of the periphery of the gap, communicating with the injection part and the gap, wherein the space is formed on at least a part of the periphery of the resin substrate, and the width in the thickness direction of the space is greater than the width in the thickness direction of the gap. Specifically, the polymerizable composition containing an isocyanate compound, a thiol compound, a polyol compound, and a photochromic compound is injected from the injection part, and the polymerizable composition is filled into the gap through the space; a step of heating the filled polymerizable composition to polymerize and harden it, thereby forming a photochromic layer (a photochromic compound-containing layer) on the resin substrate; removing the obtained laminate composed of the resin substrate and the photochromic layer; Includes:

[0014] According to the method for producing a photochromic lens using the injection molding apparatus of the present invention, a photochromic layer having a predetermined thickness can be laminated on a resin substrate, and a photochromic lens having excellent photochromic response and suppressed initial coloring can be obtained. Furthermore, the polymerizable composition can be uniformly filled into the gap formed between the substrate and the resin substrate, and a photochromic lens having excellent appearance and suppressing the inclusion of air bubbles and the occurrence of striae can be produced.

[0015] A method for manufacturing photochromic lenses using the injection molding apparatus of the present invention will be described using embodiments. The embodiments will be described using a first or second embodiment with reference to the accompanying drawings. Note that explanations of identical symbols will be omitted where appropriate. In this embodiment, "~" indicates "more than" to "less than" unless otherwise specified.

[0016] First, the injection molding apparatus used in the method for manufacturing the photochromic lens of this embodiment will be described using a first or second embodiment.

[0017] [First embodiment] As shown in the schematic cross-sectional view of Figure 1, an injection molding apparatus 10 of this embodiment includes a substantially circular substrate 12, a substantially circular resin substrate 14 arranged opposite a surface 12a of the substrate 12, a fixing member 16 for fixing the peripheral edge of the substrate 12 and the peripheral edge of the resin substrate 14, and an injection section 18 provided on the fixing member 16 for injecting a polymerizable composition into a gap 20 between the substrate 12 and the resin substrate 14. A space 22 is provided around the entire periphery of the gap 20. In this embodiment, a molded product can be obtained by polymerizing the polymerizable composition filled in the gap 20.

[0018] The substantially circular substrate 12 is not particularly limited as long as a molded body can be prepared within the gap 20, and can be made of, for example, glass, metal, resin, etc. The substantially circular substrate 12 can be used as a mold substrate, and can also be a laminate of the substrate 12 and a thin film molded body formed within the gap 20. The substrate 12 has a surface 12a facing the resin substrate 14. When the molded body is used as a laminated film of an optical lens, the surface 12a can be used as a forming surface for forming the objective surface.

[0019] The substantially circular resin substrate 14 is not particularly limited as long as a molded body can be prepared within the gap 20, but can be composed of a resin selected from poly(thio)urethane, poly(thio)urethane urea, polysulfide (e.g., polyepisulfide, polyene-polythiol polymer, polythioether, etc.), polyepoxide, polycarbonate, poly(meth)acrylate, ADC (allyl diglycol carbonate), polyolefin, cyclic polyolefin, ring-opening metathesis polymer, polyester, polysiloxane, polyamide, polyimide, etc. The substantially circular resin substrate 14 can be used to obtain a laminate (photochromic lens) together with a thin-film photochromic layer formed within the gap 20.

[0020] Since the photochromic layer is made of a thiourethane resin as described below, the resin substrate 14 is preferably made of a polyepisulfide resin, a polyurethane resin, or a polythiourethane resin, and more preferably a polyepisulfide resin or a polythiourethane resin. Examples of monomer components constituting the resin contained in the resin substrate 14 include monomer components contained in the polymerizable composition described below, and these monomer components may be the same or different.

[0021] The substantially circular resin substrate 14 has a surface 14a that faces the surface 12a of the substrate 12, and the substrate 12 and the resin substrate 14 are curved in the same direction. The surfaces (curved surfaces) 12a and 14a preferably have substantially the same radius of curvature, and the width of the gap 20 between these surfaces in the thickness direction is preferably substantially the same. The width of the gap 20 in the thickness direction is 0.1 mm to 2.5 mm, preferably 0.3 mm to 2.0 mm, more preferably 0.5 mm to 1.5 mm, and particularly preferably 0.6 mm to 1.2 mm. The lower limit of the width of the gap 20 in the thickness direction is 0.1 mm or more, preferably 0.3 mm or more, more preferably 0.5 mm or more, and particularly preferably 0.6 mm or more. The upper limit of the width of the gap 20 in the thickness direction is 2.5 mm or less, preferably 2.0 mm or less, more preferably 1.5 mm or less, and particularly preferably 1.2 mm or less. By setting the width of gap 20 in the thickness direction to be equal to or greater than the above-mentioned lower limit, the polymerizable composition flows appropriately within gap 20 and is uniformly filled, thereby reducing uneven distribution of the photochromic compound. On the other hand, by setting the width of gap 20 in the thickness direction to be equal to or less than the above-mentioned upper limit, a photochromic layer having a predetermined thickness can be laminated on resin substrate 14, and even if the concentration of the photochromic compound is increased, initial coloring can be easily suppressed, making it possible to obtain a photochromic lens with excellent photochromic response.

[0022] The gap 20 is a gap formed between the surface 14a of the resin substrate 14 and the surface 12a of the substrate 12 when they are arranged so that they face each other. Furthermore, by arranging the surface 14a of the resin substrate 14 and the surface 12a of the substrate 12 so that at least a portion of them is parallel to each other, the thickness of the photochromic layer obtained by the polymerizable composition filled in the gap 20 can be made uniform. The width in the thickness direction of the gap 20 refers to the average of the shortest distance between the surface 14a and the surface 12a, and corresponds to the thickness of the photochromic layer obtained later.

[0023] According to the manufacturing method using the injection molding apparatus 10 of this embodiment, even in the case of a gap 20 of such width, the polymerizable composition is filled through the space 22, so that the gap 20 can be filled uniformly while preventing air bubbles from being mixed in, and a photochromic lens with an excellent appearance and with reduced air bubble mixing can be manufactured. Furthermore, in conventional techniques, the photochromic layer is obtained by applying a polymerizable composition using a method such as spin coating, which tends to result in a high concentration of the photochromic compound at the periphery of the photochromic layer. In contrast, in the present embodiment, the polymerizable composition can be uniformly filled in the gap 20, thereby reducing uneven distribution of the photochromic compound.

[0024] Resin substrate 14 has a notch 24 along the entire periphery. As shown in Figure 1, injection molding apparatus 10 has a space 22 surrounded by notch 24 of resin substrate 14, substrate 12, and fixing member 16. The width i of space 22 in the substrate thickness direction is not particularly limited as long as it is greater than the width of gap 20, and the upper limit can vary appropriately depending on the thickness, strength, etc. of resin substrate 14. The width i of space 22 in the substrate diameter direction is preferably, for example, approximately 1 to 10 mm.

[0025] As shown in FIG. 1, the width ii of the space 22 in the diameter direction of the resin substrate 14 (in other words, the length from the edge of the resin substrate 14 toward the center of the resin 14) is not particularly limited as long as the space 22 is formed, but is preferably about 1 to 10 mm. The diameter iii of the resin substrate 14 is about 50 mm to 100 mm. The ratio (ii / iii) of the width ii of the space 22 in the substrate diameter direction to the diameter iii of the resin substrate 14 is greater than 0 and not more than 0.27, and preferably about 0.01 to 0.27.

[0026] As shown in FIG. 1, the space 22 is in communication with the injection portion 18 and the gap 20, and is configured so that the polymerizable composition injected from the injection portion 18 can be filled into the gap 20 via the space 22, as shown in the schematic plan view of FIG. 2. That is, the polymerizable composition of this embodiment has a relatively high viscosity as described below, and therefore tends to entrain air bubbles during filling. However, with the injection molding apparatus 10 of this embodiment, the polymerizable composition is filled into the gap 20 through the wide space 22, thereby preventing air bubbles from being mixed in.

[0027] In this embodiment, the substrate 12 and the resin substrate 14 can be used as mold substrates. In this embodiment, a laminate of the thin-film photochromic layer formed in the gap 20 and the resin substrate 14 is used as a photochromic lens, so the substrate 12 is a mold substrate having a forming surface (surface 12a) for forming an objective surface on the resin substrate 14 side, and the concave surface of the resin substrate 14 can be used as an eye surface.

[0028] The fixing member 16 is not particularly limited as long as it can position the surface 12a of the substrate 12 and the surface 14a of the resin substrate 14 facing each other, and can be made of tape, a gasket, or the like. Tape can be wrapped around the peripheral edges of the substrate 12 and the resin substrate 14 to fix these in position. It is also preferable that the surface 12a of the substrate 12 and the surface 14a of the resin substrate 14 are fixed so that at least a portion of each is parallel to each other.

[0029] Injection part 18, not shown, is provided on fixing member 16 so that the polymerizable composition can be injected into space 22. For example, it may be an opening or a joint of an injection device. The polymerizable composition can be injected into space 22 from injection part 18, and injection means such as a pipette tip, a syringe, or an automatic injection device can also be connected to injection part 18. The viscosity of the polymerizable composition used in this embodiment can be set to 5 to 1000 mPa·s, and preferably 10 to 500 mPa·s. The viscosity of the polymerizable composition can be measured at 25°C using a Brookfield viscometer.

[0030] Even with a polymerizable composition having such a viscosity, the injection molding apparatus 10 of this embodiment can uniformly fill the polymerizable composition into the gap 20 through the space 22, and can laminate a photochromic layer having a predetermined thickness on the resin substrate 14, thereby producing a photochromic lens with suppressed initial coloring and excellent photochromic response, as well as a photochromic lens with excellent appearance and suppressed inclusion of air bubbles, etc.

[0031] Although the embodiments of the present invention have been described above, these are merely examples of the present invention, and various configurations other than those described above can be adopted as long as they do not impair the effects of the present invention.

[0032] FIG. 1 shows an example in which the space 22 is surrounded by the cutout portion 24 of the resin substrate 14, the substrate 12, and the fixing member 16, but a groove with a U-shaped cross section may be provided around the entire periphery of the resin substrate 14, and the space 22 may be formed by the groove formed in the resin substrate 14 and the substrate 12. In FIG. 1, an example has been described in which the surface 12a of the substrate 12 is concave and the surface 14a of the resin substrate 14 is convex, but the surface 12a may be convex and the surface 14a may be concave.

[0033] 1, an example has been described in which the substrate 12 and the resin substrate 14 are curved, but various shapes can be adopted for the molded body depending on the application, and for example, both the substrate 12 and the resin substrate 14 may be flat plates with a substantially circular shape. That is, the resin substrate 14 may be a resin lens with curved surfaces on both sides, a resin lens with only the surface 14a being curved, or a resin flat plate with flat surfaces on both sides. The same applies to other embodiments.

[0034] 1 has been described as an example in which the space 22 is provided around the entire periphery of the resin substrate 14, but as shown in Fig. 3, the space 22 may be provided around approximately half the periphery of the resin substrate 14, or may be provided to any position selected from approximately half the periphery (1 / 2) to less than the entire periphery. In addition, the space 22 is not limited to being continuous, and a plurality of discontinuous spaces may be provided.

[0035] As shown in Fig. 4, the notches 24 may be provided on the periphery of the substrate 12 to form the spaces 22, or as shown in Fig. 5, the notches 24 may be provided on the periphery of the substrate 12 and the resin substrate 14 to form the spaces 22. Furthermore, the notches 24 may be provided alternately in the circumferential direction of the substrate 12 and the resin substrate 14.

[0036] [Second embodiment] As shown in the schematic cross-sectional view of Figure 6, the injection molding apparatus 10 of this embodiment comprises an approximately circular substrate 12, an approximately circular resin substrate 15 arranged opposite the surface 12a of the substrate 12, a fixing member 16 for fixing the peripheral edge of the substrate 12 and the peripheral edge of the resin substrate 15, and an injection section 18 provided on the fixing member 16 for injecting a polymerizable composition into the gap 20 between the substrate 12 and the resin substrate 15. A gap 20 is provided between the curved surface 12a of the substrate 12 and the curved surface 15a of the resin substrate 15 facing the curved surface 12a, and the radius of curvature b of the curved surface 15b at the periphery of the curved surface 15a of the resin substrate 15 is smaller than the radius of curvature a of the curved surface 15a surrounded by the periphery. This forms a space 23 around the periphery of the gap 20. The substantially circular substrate 12, the surface 12a, and the injection portion 18 (not shown) are the same as those in the first embodiment, and therefore a description thereof will be omitted. The curved surface 12a of the substrate 12 and the curved surface 15a of the resin substrate 15 facing the curved surface 12a are at least partially parallel to each other, and the gap 20 is provided in this parallel space.

[0037] The substantially circular resin substrate 15 is not particularly limited as long as a molded body can be prepared within the gap 20, but can be composed of a resin selected from poly(thio)urethane, poly(thio)urethane urea, polysulfide (e.g., polyepisulfide, polyene-polythiol polymer, polythioether, etc.), polyepoxide, polycarbonate, poly(meth)acrylate, ADC (allyl diglycol carbonate), polyolefin, cyclic polyolefin, ring-opening metathesis polymer, polyester, polysiloxane, polyamide, polyimide, etc. The substantially circular resin substrate 14 can form a laminate (photochromic lens) together with the thin-film photochromic layer formed within the gap 20. Since the photochromic layer (photochromic compound-containing layer) is made of a thiourethane resin as described below, the resin substrate 15 is preferably made of a urethane resin or a thiourethane resin, more preferably a thiourethane resin. Examples of monomer components constituting the resin contained in the resin substrate 15 include monomer components contained in the polymerizable composition described below, and these monomer components may be the same or different.

[0038] The substantially circular resin substrate 15 has a surface 15a that faces the surface 12a of the substrate 12, and the substrate 12 and the resin substrate 15 are curved in the same direction. The surfaces (curved surfaces) 12a and 15a have substantially the same radius of curvature, and the width of the gap 20 between these surfaces in the thickness direction is substantially the same. The width of the gap 20 in the thickness direction is 0.1 mm to 2.5 mm, preferably 0.3 mm to 2.0 mm, more preferably 0.5 mm to 1.5 mm, and particularly preferably 0.6 mm to 1.2 mm. The lower limit of the width of the gap 20 in the thickness direction is 0.1 mm or more, preferably 0.3 mm or more, more preferably 0.5 mm or more, and particularly preferably 0.6 mm or more. The upper limit of the width of the gap 20 in the thickness direction is 2.5 mm or less, preferably 2.0 mm or less, more preferably 1.5 mm or less, and particularly preferably 1.2 mm or less. By setting the width of the gap 20 within this range, a photochromic layer having a predetermined thickness can be laminated on the resin substrate 15, and initial coloring is suppressed, resulting in a photochromic lens with excellent photochromic response.

[0039] Resin substrate 15 has curved surface 15a and curved surface 15b along the entire periphery. The radius of curvature b of curved surface 15b along the periphery is different from the radius of curvature a of curved surface 15a surrounded by curved surface 15b, with radius of curvature b being smaller than radius of curvature a. As a result, width c of curved surface 15a in the thickness direction of resin substrate 15 is greater than width d of curved surface 15b along the periphery of resin substrate 15. Because the radius of curvature of surface 12a of substrate 12 is constant, a space 23 is formed around gap 20.

[0040] There are no particular limitations on the radius of curvature b of curved surface 15b as long as it is smaller than the radius of curvature a of curved surface 15a surrounded by curved surface 15b, but the radius of curvature a is preferably 100 mm to 500 mm, more preferably 150 mm to 300 mm, and the radius of curvature b is preferably 10 mm to 100 mm, more preferably 15 mm to 50 mm.

[0041] The width ii in the substrate diameter direction of the peripheral portion having the curved surface 15b is not particularly limited as long as the space 23 is formed, but is preferably about 1 mm to 10 mm. The diameter iii of the resin substrate 15 is about 50 mm to 100 mm. The ratio (ii / iii) of the width ii in the substrate diameter direction of the peripheral portion having the curved surface 15a to the diameter iii of the resin substrate 15 is greater than 0 and not more than 0.27, and preferably about 0.01 to 0.27.

[0042] According to the injection molding apparatus 10 of this embodiment, even in the case of a gap 20 of such width, the polymerizable composition can be uniformly filled into the gap 20 through the space 23, and a molded body with an excellent appearance and suppressed inclusion of air bubbles, etc. can be produced.

[0043] As shown in FIG. 6, the space 23 is in communication with the injection portion 18 and the gap 20, and is configured so that the polymerizable composition injected from the injection portion 18 can be filled into the gap 20 via the space 23, as shown in the schematic plan view of FIG. 2.

[0044] In this embodiment, the substrate 12 and the resin substrate 15 can be molded substrates. When the thin-film molded body formed in the gap 20 is used as a laminated film of an optical lens, the substrate 12 is a molded substrate having a forming surface for forming an objective surface on the resin substrate 15 side, and the concave surface of the resin substrate 15 can be used as an eye surface. Examples of the monomer components constituting the resin substrate 15 include the monomer components contained in the polymerizable composition described below, and these monomer components may be the same or different.

[0045] The viscosity of the polymerizable composition used in this embodiment can be set to 5 mPa·s to 1000 mPa·s, and preferably 10 mPa·s to 500 mPa·s.

[0046] The injection molding apparatus 10 of this embodiment can uniformly fill the polymerizable composition into the gap 20 through the space 23, even if the polymerizable composition has such a viscosity, and can produce a molded product with an excellent appearance and with reduced inclusion of air bubbles, etc.

[0047] Although the embodiments of the present invention have been described above, these are merely examples of the present invention, and various configurations other than those described above can be adopted as long as they do not impair the effects of the present invention.

[0048] In Figure 6, an example has been described in which the space 23 is provided around the entire periphery of the resin substrate 15, but the space 23 may also be provided around approximately half the periphery of the resin substrate 15, or may be provided at any position selected from approximately half the periphery (1 / 2) to less than the entire periphery.

[0049] In this embodiment, the surface 12a of the substrate 12 is a curved flat plate having approximately the same radius of curvature over the entire surface, and the resin substrate 15 is provided with a curved surface 15a and a curved surface 15b around the entire peripheral edge. However, the opposite configuration can also be achieved, where the surface of the resin substrate 15 facing the substrate 12 is a curved flat plate having approximately the same radius of curvature over the entire surface, and the surface of the substrate 12 facing the resin substrate 15 is provided with a curved surface with a large radius of curvature over the peripheral edge, thereby forming a space. Furthermore, resin substrate 15 may have curved surface 15b on its peripheral portion, and substrate 12 may also have the curved surface on its peripheral portion, with the opposing curved surfaces at the peripheral portion forming space 23. Furthermore, the curved surfaces at the peripheral portion may be provided alternately on substrate 12 and resin substrate 14 in the circumferential direction.

[0050] <Photochromic lens manufacturing method> The method for manufacturing a photochromic lens of this embodiment is carried out using the above-described injection molding apparatus 10 and includes the following steps. Step a: The polymerizable composition containing an isocyanate compound, a thiol compound, a polyol compound, and a photochromic compound is injected from injection portion 18, and the polymerizable composition is filled into gap 20 via space 22. Step b: The filled polymerizable composition is heated to polymerize and harden, thereby forming a photochromic layer on the resin substrate 14. Step c: The resulting laminate consisting of the photochromic layer and the resin substrate 14 is taken out. According to the method for manufacturing a photochromic lens using the injection molding apparatus of this embodiment, a photochromic layer containing a photochromic compound and having a predetermined thickness can be laminated on a resin substrate, and a photochromic lens with suppressed initial coloration and excellent photochromic response can be obtained. Furthermore, the polymerizable composition can be uniformly filled into the gap 20 formed between the substrate 12 and the resin substrate 14, and a photochromic lens with excellent appearance and suppressed inclusion of air bubbles and the occurrence of striae can be manufactured. Furthermore, the following step d may be included. Step d: The polymerizable composition that has been polymerized and cured in the space 22 around the periphery of the laminate is removed, and the photochromic layer obtained by polymerization and curing in the gap 20 is exposed at the end face of the laminate. This results in a laminate consisting of a photochromic layer of uniform thickness and the resin substrate 14, which can be suitably used as a photochromic lens.

[0051] Hereinafter, embodiments of the injection molding method and the method for manufacturing a molded article of the present invention will be described in detail with reference to the accompanying drawings. The same reference numerals will be omitted where appropriate. While the following description will be given using the injection molding apparatus 10 of the first embodiment, the same process can also be carried out using the injection molding apparatus 10 of the second embodiment.

[0052] [Step a] In the injection molding method of this embodiment, first, injection molding apparatus 10 of this embodiment is positioned so that injection section 18 is positioned vertically above a horizontal plane. To prepare a polarized lens, a polarizing film can be adhered to surface 14a of resin substrate 14 in advance.

[0053] The polarizing film can be made of a thermoplastic resin. Examples of the thermoplastic resin include a single layer or a laminate of multiple layers of thermoplastic polyester, thermoplastic polycarbonate, thermoplastic polyolefin, thermoplastic polyimide, thermoplastic polyamide, polyvinyl alcohol (PVA), triacetyl cellulose (TAC), etc. From the viewpoints of water resistance, heat resistance, and moldability, thermoplastic polyester and thermoplastic polycarbonate are preferred, and from the viewpoints of water resistance and weather resistance, thermoplastic polyester is more preferred.

[0054] Examples of thermoplastic polyesters include polyethylene terephthalate, polyethylene naphthalate, and polybutylene terephthalate, with polyethylene terephthalate being preferred from the viewpoints of water resistance, heat resistance, and moldability.

[0055] For the purpose of imparting polarization properties, a dichroic dye or the like can be added to the functional layer made of the thermoplastic resin. Known dichroic dyes are used. For example, they are disclosed in JP-A-61-087757, JP-A-61-285259, JP-A-62-270664, JP-A-62-275163, JP-A-1-103667, etc. Specific examples include anthraquinone-based, quinophthalone-based, and azo-based dyes.

[0056] Then, using an injection means (not shown), the polymerizable composition is injected into the space 22 from the injection part 18. The injection speed is appropriately set depending on the viscosity of the polymerizable composition, and may be changed so that the filling speed in the space 22 becomes uniform. The viscosity of the polymerizable composition can be set to 5 mPa·s to 1000 mPa·s, preferably 10 mPa·s to 500 mPa·s.

[0057] As shown in the schematic plan view of Figure 2, the polymerizable composition injected into space 22 moves mainly downward within space 22, and when it reaches the bottom, moves into gap 20. Because the composition is mainly filled from the bottom into gap 20, a molded product with excellent appearance and reduced inclusion of air bubbles can be obtained, and because the composition is filled uniformly in a certain direction, a molded product with reduced occurrence of striae can be obtained.

[0058] The polymerizable composition used in this embodiment contains an isocyanate compound, a thiol compound, a polyol compound, and a photochromic compound.

[0059] (Isocyanate compounds) Examples of the isocyanate compound include aliphatic isocyanate compounds, alicyclic isocyanate compounds, aromatic isocyanate compounds, heterocyclic isocyanate compounds, and aromatic aliphatic isocyanate compounds, and these compounds may be used alone or in combination. These isocyanate compounds may include dimers, trimers, and prepolymers. Examples of these isocyanate compounds include the compounds exemplified in WO2011 / 055540.

[0060] In this embodiment, it is more preferable that the isocyanate compound is at least one selected from pentamethylene diisocyanate, hexamethylene diisocyanate, xylylene diisocyanate, bis(isocyanatocyclohexyl)methane, isophorone diisocyanate, 2,5-bis(isocyanatomethyl)bicyclo-[2.2.1]-heptane, 2,6-bis(isocyanatomethyl)bicyclo-[2.2.1]-heptane, tolylene diisocyanate, 4,4'-diphenylmethane diisocyanate, and phenylene diisocyanate.

[0061] (Thiol compounds) Examples of the thiol compound include a polythiol compound having two or more mercapto groups, a hydroxythiol compound having one or more mercapto groups and one or more hydroxyl groups, and the like, and these compounds are used alone or in combination. Examples of these thiol compounds include the compounds exemplified in WO2016 / 125736.

[0062] The polythiol compound is preferably 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane, 5,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 4,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 4,8-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, pentaerythritol tetrakis(2- and at least one selected from the group consisting of 2,5-dimercaptomethyl-1,4-dithiane, 1,1,3,3-tetrakis(mercaptomethylthio)propane, 4,6-bis(mercaptomethylthio)-1,3-dithiane, and 2-(2,2-bis(mercaptomethylthio)ethyl)-1,3-dithietane. The thiol compound is preferably a polythiol compound having two or more mercapto groups.

[0063] In this embodiment, the molar ratio of thiol groups in the thiol compound to isocyanato groups in the isocyanate compound is within a range of 0.8 to 1.2, preferably within a range of 0.85 to 1.15, and more preferably within a range of 0.9 to 1.1. Within the above range, a resin suitable for use as an optical material, particularly as a material for plastic eyeglass lenses, can be obtained.

[0064] (Polyol compound) As the polyol compound, a known compound can be used within the scope of the effects of the present invention, for example, polymer (ii) described in WO2018 / 158813 can be used. In this embodiment, it is preferable to use a compound represented by the following general formula (iia):

[0065] [ka]

[0066] In general formula (iia), R1 and R2 represent a hydrogen atom or an alkyl group having 1 to 18 carbon atoms, and at least one of them is a hydrogen atom. Multiple R1s may be the same or different, and multiple R2s may be the same or different. m represents an integer of 15 to 500, preferably 30 to 500. The compound represented by general formula (iia) has a number average molecular weight of 150 or more, preferably 200 or more.

[0067] As the compound represented by general formula (iia), a compound represented by the following general formula (iia-1) can be used: Specifically, in general formula (ii), when R1 is an alkylene (carbon number: C2 to C20) glycolate group, A1 is a polyalkylene (carbon number: C2 to C20) glycol chain, R2 is an oxypropylene group, A2 is a polyethylene glycol chain, R3 is a hydroxyethylene group, and n is the valence of the propylene glycolate group, 2, the compound is represented by the following general formula (iia-1).

[0068] [ka]

[0069] In general formula (iia-1), R3 and R4 represent a hydrogen atom or an alkyl group having 1 to 18 carbon atoms, and at least one of them is a hydrogen atom. a+c represents an integer of 2 or more and 600 or less, preferably 2 or more and 400 or less, and b represents an integer of 1 or more and 300 or less, preferably 1 or more and 100 or less. Multiple R3s and R4s may be the same or different.

[0070] Examples of such compounds include the Pluronic series, a registered trademark of BASF. The structures of compounds included in Pluronic are shown in Non-Patent Document 1. The terminal hydroxyl group of the compound represented by general formula (iia) may react with a polymerizable compound such as an isocyanate compound.

[0071] In this embodiment, the polyol compound may be contained in an amount of 0.01 to 50 parts by weight, preferably 0.05 to 20 parts by weight, and more preferably 0.1 to 10 parts by weight, per 100 parts by weight of the polymerization reactive compounds (isocyanate compounds and thiol compounds). By containing the polyol compound, photochromic response can be improved.

[0072] (Photochromic compounds) Photochromic compounds include compounds whose absorption characteristics (absorption spectrum) change with respect to light of a specific wavelength. Known photochromic compounds can be used, and examples thereof include compounds derived from compounds such as naphthopyran, chromene, spiropyran, spirooxazine and thiospiropyran, benzopyran, stilbene, azobenzene, thioindigo, bisimidazole, spirodihydroindolizine, quinine, perimidine spirocyclohexadienone, viologen, fulgide, fulgimide, diarylethene, hydrazine, aniline, aryl disulfide, aryl thiosulfonate, spiroperimidine, and triarylmethane. In this embodiment, it is preferable to use a naphthopyran derivative as the photochromic compound.

[0073] In this embodiment, it is preferable to use at least one photochromic compound selected from the general formula (c1) and the general formula (c2). PC-L-Chain (c1) PC-L-Chain-L'-PC' (c2) PC and PC' represent monovalent groups derived from compounds of general formulae (1) to (4). PC and PC' may be the same or different.

[0074] [ka]

[0075] In formulas (1) to (4), R1 to R 18 represents a hydrogen atom, a halogen atom, a carboxyl group, an acetyl group, a formyl group, an optionally substituted aliphatic group having 1 to 20 carbon atoms, an optionally substituted alicyclic group having 3 to 20 carbon atoms, or an optionally substituted aromatic organic group having 6 to 20 carbon atoms, and may be the same or different. These aliphatic groups, alicyclic groups, or aromatic organic groups may contain an oxygen atom or a nitrogen atom. Any one of the groups contained in the compounds represented by general formulas (1) to (4) is bonded to the divalent organic group L or L'.

[0076] Examples of the optionally substituted aliphatic group having 1 to 20 carbon atoms include a linear or branched chain alkyl group having 1 to 10 carbon atoms, a linear or branched chain alkoxy group having 1 to 10 carbon atoms, a linear or branched chain alkenyl group having 2 to 10 carbon atoms, a hydroxyalkyl group having 1 to 10 carbon atoms, a hydroxyalkoxy group having 1 to 10 carbon atoms, an alkyl group having 1 to 10 carbon atoms substituted with an alkoxy group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms substituted with an alkoxy group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 5 carbon atoms, a dihaloalkyl group having 1 to 5 carbon atoms, a trihaloalkyl group having 1 to 5 carbon atoms, an alkylamino group having 1 to 10 carbon atoms, an aminoalkyl group having 1 to 10 carbon atoms, and a linear or branched chain alkoxycarbonyl group having 1 to 20 carbon atoms. Examples of the optionally substituted alicyclic group having 3 to 20 carbon atoms include a cycloalkyl group having 3 to 20 carbon atoms and a bicycloalkyl group having 6 to 20 carbon atoms.

[0077] Examples of the optionally substituted aromatic organic group having 6 to 20 carbon atoms include a phenyl group, an alkoxyphenyl group having 7 to 16 carbon atoms, an arylamino group, a diarylamino group, an aryl alkylamino group having 1 to 5 carbon atoms, a cyclic amino group, an arylcarbonyl group, and an aroyl group.

[0078] R1 and R2 are preferably hydrogen atoms; halogen atoms; aliphatic groups having 1 to 20 carbon atoms which may be substituted, such as a straight-chain or branched-chain alkyl group having 1 to 10 carbon atoms, a straight-chain or branched-chain alkoxy group having 1 to 10 carbon atoms, a hydroxyalkoxy group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms substituted with an alkoxy group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 5 carbon atoms, a dihaloalkyl group having 1 to 5 carbon atoms, a trihaloalkyl group having 1 to 5 carbon atoms, or an alkylamino group having 1 to 5 carbon atoms; Examples include aromatic organic groups having 6 to 20 carbon atoms, which may be substituted, such as a phenyl group, an alkoxyphenyl group having 7 to 16 carbon atoms, a dialkylamino group having 1 to 5 carbon atoms, an arylamino group, a diarylamino group, an aryl alkylamino group having 1 to 5 carbon atoms, and a cyclic amino group. R1 and R2 may be the same or different.

[0079] R3 is preferably a hydrogen atom; a halogen atom; a carboxyl group; an acetyl group; aliphatic groups having 1 to 20 carbon atoms which may be substituted, such as a linear or branched alkyl group having 1 to 10 carbon atoms, a linear or branched alkenyl group having 2 to 10 carbon atoms, a linear or branched alkoxy group having 1 to 10 carbon atoms, a hydroxyalkyl group having 1 to 10 carbon atoms, an alkyl group having 1 to 10 carbon atoms substituted with an alkoxy group having 1 to 10 carbon atoms, an aminoalkyl group having 1 to 10 carbon atoms, and a linear or branched alkoxycarbonyl group having 1 to 20 carbon atoms; an optionally substituted alicyclic group having 3 to 20 carbon atoms, such as a cycloalkyl group having 3 to 20 carbon atoms and a bicycloalkyl group having 6 to 20 carbon atoms; Examples include aromatic organic groups having 6 to 20 carbon atoms, such as an arylcarbonyl group, a formyl group, and an aroyl group, which may be substituted. R4 is preferably a hydrogen atom; a halogen atom; a carboxyl group; an acetyl group; or a formyl group. aliphatic groups having 1 to 20 carbon atoms which may be substituted, such as a linear or branched alkyl group having 1 to 10 carbon atoms, a linear or branched alkenyl group having 2 to 10 carbon atoms, a linear or branched alkoxy group having 1 to 10 carbon atoms, a hydroxyalkyl group having 1 to 10 carbon atoms, an alkyl group having 1 to 10 carbon atoms substituted with an alkoxy group having 1 to 10 carbon atoms, an aminoalkyl group having 1 to 10 carbon atoms, and a linear or branched alkoxycarbonyl group having 1 to 20 carbon atoms; an optionally substituted alicyclic group having 3 to 20 carbon atoms, such as a cycloalkyl group having 3 to 20 carbon atoms and a bicycloalkyl group having 6 to 20 carbon atoms; Examples include aromatic organic groups having 6 to 20 carbon atoms which may be substituted, such as an arylcarbonyl group, an aroyl group, a phenyl group, an alkoxyphenyl group having 7 to 16 carbon atoms, a dialkoxyphenyl group having 1 to 10 carbon atoms, an alkylphenyl group having 1 to 10 carbon atoms, and a dialkylphenyl group having 1 to 10 carbon atoms.

[0080] R3 and R4 may be bonded to each other. When R3 and R4 are bonded to each other to form a ring structure, examples include general formula (5) or (6). The dotted line represents the bond between the carbon atom to which R3 is bonded and the carbon atom to which R4 is bonded.

[0081] [ka]

[0082] R5, R6, R7, R8, R9, R 10 , R 14 , R 15 , R 16 represents a functional group similar to R1 and R2. The plural R5 to R7 may be the same or different.

[0083] R 11 Preferably, a hydrogen atom; a halogen atom; optionally substituted aliphatic groups having 1 to 20 carbon atoms, such as linear or branched alkyl groups having 1 to 20 carbon atoms, haloalkyl groups having 1 to 5 carbon atoms, dihaloalkyl groups having 1 to 5 carbon atoms, and trihaloalkyl groups having 1 to 5 carbon atoms; alicyclic groups having 3 to 20 carbon atoms which may be substituted, such as a cycloalkyl group having 3 to 20 carbon atoms, a bicycloalkyl group having 6 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms substituted with an alkyl group having 1 to 5 carbon atoms, and a bicycloalkyl group having 6 to 20 carbon atoms substituted with an alkyl group having 1 to 5 carbon atoms; Examples include aromatic organic groups having 6 to 20 carbon atoms that may be substituted, such as an aryl group substituted with an alkyl group having 1 to 5 carbon atoms; and the like.

[0084] R 12 and R 13 Preferably, a hydrogen atom; a halogen atom; Examples of the alkyl group include an aliphatic group having 1 to 20 carbon atoms, which may be substituted, such as an alkyl group having 1 to 10 carbon atoms and an alkylalkoxycarbonyl group having 1 to 5 carbon atoms; an alicyclic group having 3 to 20 carbon atoms, which may be substituted, such as a cycloalkyl group having 5 to 7 carbon atoms; and the like.

[0085] R 17 and R 18 Preferably, a hydrogen atom; a halogen atom; Examples of the alkyl group include an aliphatic group having 1 to 20 carbon atoms, which may be substituted, such as a linear or branched alkyl group having 1 to 10 carbon atoms, and a hydroxyalkyl group having 1 to 10 carbon atoms; an alicyclic group having 3 to 20 carbon atoms, which may be substituted, such as a cycloalkyl group having 5 to 7 carbon atoms; and the like.

[0086] L and L' in general formula (c1) or (c2) represent a divalent organic group containing at least one group selected from an oxyethylene chain, an oxypropylene chain, a (thio)ester group, and a (thio)amide group. Specifically, L and L' are represented by the general formulas (7) to (13). L and L' may be the same or different.

[0087] [ka]

[0088] In formulas (7) to (13), Y represents oxygen or sulfur. R 19 represents hydrogen or a linear or branched alkyl group having 1 to 10 carbon atoms. R 20 represents a linear or branched alkyl group having 1 to 10 carbon atoms. p represents an integer of 0 to 15, and r represents an integer of 0 to 10.

[0089] Q represents a linear or branched alkylene group having 1 to 10 carbon atoms, an alkenylene group having 1 to 10 carbon atoms, a divalent group derived from an aryl group substituted at the 1,2-, 1,3-, or 1,4-positions, a divalent group derived from a substituted heteroaryl group, or the like. *1 and *2 represent bonds, *1 bonds to a monovalent or divalent organic group represented by "Chain", and *2 bonds to a monovalent organic group represented by PC or PC'.

[0090] "Chain" in general formula (c1) or (c2) represents a monovalent or divalent organic group containing at least one chain selected from a polysiloxane chain and a polyoxyalkylene chain. Examples of the polysiloxane chain include a polydimethylsiloxane chain, a polymethylphenylsiloxane chain, and a polymethylhydrosiloxane chain. Examples of the polyoxyalkylene chain include a polyoxyethylene chain, a polyoxypropylene chain, and a polyoxyhexamethylene chain.

[0091] in particular, When the photochromic compound is of general formula (c1), "Chain" represents a monovalent organic group of general formula (14) or (15).

[0092] [ka]

[0093] When the photochromic compound is of general formula (c2), "Chain" represents a divalent organic group of general formula (16) or (17).

[0094] [ka]

[0095] In formulas (14) to (17), R 21 represents a linear or branched alkyl group having 1 to 10 carbon atoms. R 22represents a linear or branched alkyl group having 1 to 10 carbon atoms. R 23 represents hydrogen, a methyl group, or an ethyl group. n represents an integer of 4 to 75, and m represents an integer of 1 to 50. q represents an integer of 1 to 3. *3 and *4 represent bonds, *3 is bonded to the divalent organic group represented by L, and *4 is bonded to the divalent organic group represented by L'.

[0096] The photochromic compound (C) of this embodiment can be obtained by the methods described in WO2009 / 146509, WO2010 / 20770, WO2012 / 149599, and WO2012 / 162725.

[0097] Examples of the photochromic compound of this embodiment include Reversacol Humber Blue (polydimethylsiloxane chain, naphthopyran-based chromophore (general formula 3)), Reversacol Calder Blue (polydimethylsiloxane chain, naphthopyran-based chromophore (general formula 3)), Reversacol Trent Blue (polydimethylsiloxane chain, naphthopyran-based chromophore (general formula 3)), Reversacol Pennine Green (polydimethylsiloxane chain, naphthopyran-based chromophore (general formula 3)), Reversacol Heath Green (polyoxyalkylene chain, naphthopyran-based chromophore (general formula 3)), Reversacol Chilli Red (polydimethylsiloxane chain, naphthopyran-based chromophore (general formula 3)), Reversacol Wembley Grey (polyoxyalkylene chain, naphthopyran-based chromophore (general formula 3)), Reversacol Cayenne (polydimethylsiloxane chain, naphthopyran-based chromophore (general formula 3)), and Reversacol Cayenne (polydimethylsiloxane chain, naphthopyran-based chromophore (general formula 3)). Red (polyoxyalkylene chain, naphthopyran-based chromophore (general formula 3)), Reversacol Jalapeno Red (polyoxyalkylene chain, naphthopyran-based chromophore (general formula 3)), Reversacol Marine Blue (polyoxyalkylene chain, naphthopyran-based chromophore (general formula 3)), Reversacol Adriatic Blue (polyoxyalkylene chain, naphthopyran-based chromophore (general formula 3)), Examples include Reversacol Mendip Green (polyoxyalkylene chain, naphthopyran-based chromophore (general formula 3)), and the like, and these can be used alone or in combination of two or more.

[0098] From the viewpoint of the effects of the present invention, the polymerizable composition of the present embodiment may contain the photochromic compound in an amount of 100 ppm to 10,000 ppm, preferably 1,000 ppm to 8,000 ppm, and more preferably 2,500 ppm to 6,000 ppm. The weight ratio of the polyol compound to the photochromic compound is not particularly limited, but the photochromic compound is preferably 0.01 to 100 parts by weight, more preferably 1 to 10 parts by weight, per 100 parts by weight of the polyol compound. The photochromic compound may be added as a premix of the photochromic compound and a polyisocyanate compound. The total amount of the polyisocyanate compound used in this embodiment includes the amount of the polyisocyanate compound used in the premix.

[0099] [Other ingredients] The polymerizable composition of the present embodiment may contain, in addition to the above components, an adhesion improver, a polymerization catalyst, an internal mold release agent, an ultraviolet absorber, and the like. The polymerizable composition can be obtained by mixing the above components in a predetermined manner.

[0100] [Step b] The polymerizable composition filled in the spaces 22 and gaps 20 in step a is heated to polymerize and harden, forming a resin layer on the resin substrate 14 and obtaining a laminate. The polymerization conditions are not limited as they vary depending on the type and amount of components, the type and amount of catalyst, the shape of the mold, etc., but are generally carried out at a temperature of approximately -50 to 150°C for 1 to 50 hours.

[0101] [Process c] After step b, the laminate consisting of the resin layer (photochromic-containing layer) and the resin substrate 14 is released from the substrate 12 and the fixing member 16, and the laminate is taken out.

[0102] [Step d] Since the obtained laminate has thick portions at its periphery that have hardened in the spaces 22, the method may include a step of removing the polymerizable composition that has been polymerized and hardened in the spaces 22 at the periphery of the laminate, and exposing the photochromic layer obtained by polymerization and hardening in the spaces 22 at the edge of the laminate. The method for removing part of the hardened polymerizable composition is not particularly limited. For example, a patternless edger Le 1000 Express manufactured by NIDEK Corporation may be used to grind with a high-speed rotary blade, and the polymerizable composition at the periphery may be scraped off until the photochromic layer is exposed on the ground surface. That is, since the laminate has thick portions at its periphery that have hardened within the space 22, the thick portions can be scraped off as appropriate depending on the application. Thereafter, annealing or the like is carried out to obtain a photochromic lens.

[0103] [Photochromic lenses] In the manufacturing method of this embodiment, a photochromic lens 30 shown in Fig. 7 is prepared. The photochromic lens 30 includes a photochromic layer 32 having an objective surface 32a, and a resin layer 36 (resin substrate 14). The photochromic layer 32 has protrusions 34 on its periphery, and the protrusions 34 are embedded in and integrated with the resin layer 36. The thickness of the approximately circular center of the photochromic layer 32 in this embodiment is 0.1 to 2.5 mm, preferably 0.3 to 2.0 mm, more preferably 0.5 to 1.5 mm, and particularly preferably 0.6 to 1.2 mm. The lower limit of the thickness of the approximately circular center of the photochromic layer 32 is 0.1 mm or more, preferably 0.3 mm or more, more preferably 0.5 mm or more, and particularly preferably 0.6 mm or more. The upper limit of the thickness of the approximately circular center of the photochromic layer 32 is 2.5 mm or less, preferably 2.0 mm or less, more preferably 1.5 mm or less, and particularly preferably 1.2 mm or less. In this embodiment, the thickness of the protruding portions 34 on the periphery of the photochromic layer 32 is greater than the thickness of the photochromic layer 32 in the portion surrounded by the protruding portions 34 .

[0104] The photochromic lens 30 of this embodiment can be used by polishing it along the dotted line portion shown in Figure 7. That is, the photochromic layer 32 is exposed at the end face of the photochromic lens 30. In this case, the four-point average thickness of the peripheral portion of photochromic layer 32 is preferably 0.1 to 2.5 mm, more preferably 0.3 to 2.0 mm, even more preferably 0.5 to 1.5 mm, and especially preferably 0.6 to 1.2 mm. The lower limit of the thickness of the approximately circular center portion of photochromic layer 32 is preferably 0.1 mm or more, more preferably 0.3 mm or more, even more preferably 0.5 mm or more, and particularly preferably 0.6 mm or more. Furthermore, the difference between the four-point average thickness of the peripheral portion of the photochromic layer 32 and the thickness of the approximately circular center portion of the photochromic layer is preferably 0.3 mm or less, more preferably 0.25 mm or less, and even more preferably 0.2 mm or less.

[0105] The thickness (20° C.) of the photochromic layer 32 can be measured using a dial thickness gauge SM-130LW manufactured by TECLOCK Corporation or the like.

[0106] Furthermore, depending on the application, the eye surface 36a of the resin layer 36 can be polished. The photochromic lens 30 of this embodiment has suppressed initial coloring, and has an initial luminous transmittance (%) measured under the conditions for evaluating photochromic performance below, in a state where the lens is not irradiated with light and the photochromic compound does not develop color, of 80% to 100%, and preferably 85% to 100%. (Dimming performance evaluation) Using a xenon lamp (180 W) light source, the molded sample was allowed to develop color for 15 minutes under conditions of a temperature of 23°C and an ultraviolet intensity of 50,000 lux (lx) measured with an integrating actinometer, and the color density was confirmed. Light source: Ushio Electric Co., Ltd. MS-35AAF / FB Instantaneous multi-photometering system: Otsuka Electronics MSPD-7700

[0107] Although the embodiments of the present invention have been described above, these are merely examples of the present invention, and various configurations other than those described above can be adopted as long as they do not impair the effects of the present invention.

[0108] In Figure 7, an example is shown in which the photochromic layer 32 and the resin layer 36 are curved, but various shapes can be adopted for the molded body depending on the application.For example, the photochromic layer 32 and the resin layer 36 may both be flat plates with an approximately circular shape.

[0109] In Figure 7, an example is shown in which the protrusion 34 is provided around the entire periphery of the photochromic layer 32, but it may also be provided around approximately half the periphery of the photochromic layer 32, or may be provided up to any position selected from approximately half the periphery (1 / 2) to less than the entire periphery.

[0110] Although the embodiments of the present invention have been described above, these are merely examples of the present invention, and various configurations other than those described above can be adopted as long as they do not impair the effects of the present invention. [Example]

[0111] The present invention will be described in more detail below with reference to examples, but the present invention is not limited to these examples.

[0112] (1) Evaluation and measurement of photochromic lenses (molded samples) In the performance test of the molded product samples, the color tone and light resistance after decolorization were evaluated by the following methods. Maximum color density at 23°C: Using an Otsuka Electronics instant multi-photometer MSPD-7700 equipped with an Ushio Electric MS-35AAA / FB2000-O xenon lamp as an excitation light source, the obtained molded product sample was irradiated with excitation light for 15 minutes at a temperature of 23°C and an illuminance of 50,000 lux. After 15 minutes, the spectral transmittance was measured, and the luminous transmittance was calculated based on ISO 8980-3. [Initial color value (also called initial luminous transmittance)] A: Luminous transmittance (%) 85% or more B: Visual transmittance (%) 80% or more and less than 85% C: Visual transmittance (%) 70% or more and less than 80%

[0113] [Maximum color density at 23°C] A: Visual transmittance (%) 9% or more and less than 13% B: Visual transmittance (%) 13% or more and less than 17% C: Visual transmittance (%) 17% or more and less than 21% D: Visual transmittance (%) 21% or more and less than 25% E: Luminous transmittance (%) 25% or more

[0114] [Fading speed] The molded sample was irradiated with light at 23°C for 15 minutes using a Ushio Inc. MS-35AAF / FB xenon lamp light source (illuminance 50,000 lux). After the light irradiation was stopped, the time required for the absorbance of the molded sample at 550 nm to recover to the midpoint of the absorbance before and after color development was measured. This time was taken as the color fading rate and evaluated according to the following criteria. Molded sample samples with low luminous transmittance during color development and fast color fading rate were judged to have good photochromic performance. A: 60 seconds or less B: Over 60 seconds

[0115] [Occurrence of striae] The produced molded sample was projected with a high-pressure mercury lamp (light source model OPM-252HEG: manufactured by Ushio Inc.), and the transmitted image was visually observed for the presence or absence of striae, and evaluated according to the following criteria. ○: There were no striae at all. △: Partial or several striae were present. Striae could not be seen with the naked eye but could be seen under a mercury lamp. △-×: 1 to 9 striae were observed throughout the area. Striae could not be seen with the naked eye but could be seen under a mercury lamp. ×: There were striae throughout the entire area or 10 or more striae. The striae were clearly visible to the naked eye. XX: There were striae throughout the area or 15 or more striae. The striae were clearly visible to the naked eye.

[0116] Thickness The thicknesses of the photochromic layer and the resin substrate were measured at the point where the distance between the front and back surfaces of the molded sample was shortest, and this was taken as the thickness (mm) at the approximate center of the molded sample. The thickness of the photochromic layer was also measured at four equally spaced points on a concentric circle 21 mm away from the approximate center of the molded sample, and the average value was taken as the average thickness (mm) of the edge portion. The thickness of the photochromic layer measured above at approximately the center and at four edge points was calculated, and the value obtained by subtracting the thinnest thickness (mm) from the thickest thickness (mm) was taken as the five-point thickness variation (mm). The thickness was measured using a dial thickness gauge SM-130LW manufactured by TECLOCK.

[0117] [Color unevenness] The molded sample was left under sunlight for 1 minute, and then the appearance of the molded sample was visually inspected and evaluated according to the following evaluation criteria. Yes: The color appeared darker around the periphery of the lens than near the center. None: There appeared to be no difference in color density between the approximate center and the periphery of the lens.

[0118] (2) Raw materials for photochromic lenses In the examples, the following raw materials were used: (Polyol) Polyol A: Polyethylene glycol, Polypropylene glycol, Polyethylene glycol (Pluronic L64, manufactured by BASF) Polyol B: Polyoxyethylene polyoxypropylene glycol (Pluronic F127, manufactured by BASF)

[0119] (Photochromic compounds) Photochromic compound D1: a mixture of the following compounds: Reversacol Wembley Gray:200ppm Reversacol Jalapeno Red:200ppm Reversacol Marine Blue: 200 ppm Reversacol Adriatic Blue:500ppm Reversacol Mendip Green:800ppm

[0120] Photochromic compound D2: a mixture of the following compounds: Reversacol Wembley Gray:360ppm Reversacol Heath Green: 600 ppm Reversacol Peacock Blue:300ppm Reversacol Jalapeno Red: 24 ppm

[0121] Photochromic compound D3: a mixture of the following compounds: Reversacol Wembley Gray:180ppm Reversacol Cayenne Red: 300 ppm Reversacol Jalapeno Red:160ppm Reversacol Mendip Green:800ppm

[0122] (3) Fabrication and evaluation of photochromic lenses [Example 1] (Creation of Resin Substrate S1 and Injection Molding Apparatus 10) A mixed solution was prepared by adding 0.035 parts by weight of dibutyltin dichloride, 0.1 parts by weight of ZelecUN manufactured by STEPAN, 50.6 parts by weight of a mixture of 2,5-bis(isocyanatomethyl)bicyclo-[2.2.1]-heptane and 2,6-bis(isocyanatomethyl)bicyclo-[2.2.1]-heptane, 1.5 parts by weight of Viosob583 manufactured by Kyodo Pharmaceutical Co., Ltd. as an ultraviolet absorber, and 0.00005 parts by weight of PlastBlue8514 manufactured by Arimoto Chemical Industry Co., Ltd. This mixed solution was stirred at 25°C for 1 hour to completely dissolve the solution. Thereafter, 25.5 parts by weight of a thiol composition containing 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane and 23.9 parts by weight of a thiol composition containing pentaerythritol tetrakis(3-mercaptopropionate) were added to this prepared solution, and the mixture was stirred at 25°C for 30 minutes to obtain a homogeneous solution (polymerizable composition for optical materials). This polymerizable composition for optical materials was degassed at 600 Pa for 1 hour and filtered through a 1 μm PTFE filter to obtain a prepared solution. A casting mold was prepared by tape-attaching a front glass mold (concave surface facing the back glass mold, radius 215.80 mm) to a back glass mold (convex surface facing the front glass mold, radius 75.53 mm) facing each other. A liquid mixture was poured into the gap between the molds (6 mm separation at the approximate circular centers), and the temperature was raised from 25°C to 120°C over 16 hours. The lens was cooled to room temperature and removed from the glass mold, yielding a lens with a diameter of 81 mm. This lens was machined to a diameter of 75 mm, and a 7 mm cutout was made from the convex surface (surface 14a) and a 2 mm cutout from the edge (peripheral edge) of the 11 mm thick edge to produce a resin substrate S1 (resin substrate 14) with a notch 24 around the entire circumference. The thickness of the approximate circular center of the resin substrate S1 was 6 mm. A glass mold with a concave surface (surface 12a) of 215.80 mm radius was used as the substrate 12. The ends of the substrate 12 and the ends of the resin substrate S1 were fixed with tape (fixing member 16) so that the concave surface (surface 12a) of the substrate 12 faced the convex surface (surface 14a) of the resin substrate S1, creating an injection molding device 10 with a gap 20. The center distance of the gap 20 was 0.5 mm. In the injection molding device 10, a space 22 was formed around the entire periphery of the gap 20, surrounded by the tape (fixing member 16), the concave surface (surface 12a) of the substrate 12, and a cutout portion 24. An opening (injection portion 18) communicating with the space 22 was formed in the fixing member 16.

[0123] (Creating photochromic lenses) A master liquid was prepared in advance by dissolving 0.02 parts by weight of Reversacol Wembley Grey manufactured by Vivimed, 0.02 parts by weight of Reversacol Jalapeno Red manufactured by Vivimed, 0.02 parts by weight of Reversacol Marine Blue manufactured by Vivimed, 0.05 parts by weight of Reversacol Adriatic Blue manufactured by Vivimed, and 0.08 parts by weight of Reversacol Mendip Green manufactured by Vivimed, and 0.075 parts by weight of HOSTAVIN PR-25 as an ultraviolet absorber, in 9.73 parts by weight of a composition containing 2,5-bis(isocyanatomethyl)bicyclo-[2.2.1]-heptane and 2,6-bis(isocyanatomethyl)bicyclo-[2.2.1]-heptane. 10 parts by weight of the obtained master liquid was added to 30.28 parts by weight of a composition containing 2,5-bis(isocyanatomethyl)bicyclo-[2.2.1]-heptane and 2,6-bis(isocyanatomethyl)bicyclo-[2.2.1]-heptane and stirred. To this was added 2.52 parts by weight of Adeka Pluronic L-64 manufactured by Adeka Corporation, 0.4 parts by weight of Polyflow KL-100 manufactured by Kyoeisha Chemical, and 0.05 parts by weight of JP-506H manufactured by Johoku Chemical Industry Co., Ltd. as an acidic phosphate ester, and stirred for 30 minutes at a temperature between 15°C and 20°C (mixing process A). To the mixture obtained in the mixing step A, 19.97 parts by weight of pentaerythritol tetrakis(3-mercaptopropionate) and 27.23 parts by weight of 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane were added, and the mixture was stirred at 15°C to 20°C for 15 minutes (mixing step B). A solution was prepared by adding 0.015 parts by weight of dimethyltin dichloride to 10 parts by weight of a composition containing 2,5-bis(isocyanatomethyl)bicyclo[2.2.1]heptane and 2,6-bis(isocyanatomethyl)bicyclo[2.2.1]heptane. This solution was added to the mixture obtained in mixing step B and stirred for 15 minutes between 15 and 20°C to obtain a polymerizable composition (mixing step C). The viscosity of this polymerizable composition (B-type viscometer, 25°C, 60 rpm, rotor number 2) was 48.5 mPa·s. The polymerizable composition was then stirred and degassed for 1 hour and 30 minutes at a temperature between 15°C and 20°C under a reduced pressure of 400 Pa or less, and then filtered using a 1.0 μm PTFE filter. The resulting polymerizable composition was injected into the gap 20 between the glass mold (substrate 12) and the resin substrate S1 (resin substrate 14) at a rate of 30 ml / min through an opening (injection section 18) located at the top of the injection molding device 10 using an injection tool equipped with a pipette tip. After casting, the temperature was raised from 10°C to 130°C over 24 hours. The lens was cooled to room temperature and removed from the glass mold (substrate 12), yielding a lens (approximately circular center thickness: 6.7 mm) in which a photochromic layer was laminated on the resin substrate S1. The resin substrate S1 was then scraped so that the thickness of the resulting lens at the approximately circular center was 1.1 mm, yielding a photochromic lens. The obtained photochromic lenses (molded samples) were subjected to the evaluation and measurement described above in (1). The results are shown in Table 1. The photochromic lenses obtained were colorless and transparent, and exhibited excellent photochromic properties, developing color immediately when placed under sunlight and losing color when the light was blocked. Furthermore, no fine aggregates or striae were observed, and the lenses had a good appearance.

[0124] [Example 2] When preparing the resin substrate, 50.6 parts by weight of a mixture of 2,5-bis(isocyanatomethyl)bicyclo-[2.2.1]-heptane and 2,6-bis(isocyanatomethyl)bicyclo-[2.2.1]-heptane was replaced with 52.0 parts by weight of xylylene diisocyanate, 25.5 parts by weight of a thiol composition containing 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane, and 23.9 parts by weight of a thiol composition containing pentaerythritol tetrakis(3-mercaptopropionate) was replaced with 48.0 parts by weight of a 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane composition, and resin substrate S2 was used as resin substrate 14. A photochromic lens having a photochromic layer laminated on resin substrate 14 was obtained by the same operation as in Example 1. The photochromic lenses (molded samples) thus obtained were subjected to the evaluation and measurement described above in (1). The results are shown in Table 1.

[0125] [Example 3] When creating a resin substrate, 50.6 parts by weight of a mixture of 2,5-bis(isocyanatomethyl)bicyclo-[2.2.1]-heptane and 2,6-bis(isocyanatomethyl)bicyclo-[2.2.1]-heptane, and 50.6 parts by weight of xylylene diisocyanate; 25.5 parts by weight of a thiol composition containing 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane and 23.9 parts by weight of a thiol composition containing pentaerythritol tetrakis(3-mercaptopropionate), 49.4 parts by weight of a mixture of 5,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 4,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, and 4,8-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, A photochromic lens having a photochromic layer laminated on a resin substrate S3 was obtained in the same manner as in Example 1, except that the resin substrate S3 was used as the resin substrate 14. The photochromic lenses (molded samples) thus obtained were subjected to the evaluation and measurement described above in (1). The results are shown in Table 1.

[0126] [Example 4] (Creating a resin substrate) In 100.0 parts by weight of bis(2,3-epithiopropyl)disulfide, 0.1 parts by weight of N,N-dimethylcyclohexylamine, 0.02 parts by weight of N,N-dicyclohexylmethylamine, and 1.1 parts by weight of TINUVIN PS manufactured by BASF were dissolved, and further, 10.0 parts by weight of a mixture mainly composed of 4,8-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 4,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, and 5,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane was mixed and stirred at 20°C for 30 minutes to prepare a prepared solution. This prepared solution was degassed at 600 Pa for 1 hour and filtered through a 1 μm PTFE filter to obtain a prepared solution. The obtained prepared liquid was polymerized and cured in the same manner as in Example 1 to obtain a resin substrate S4 (resin substrate 14). Using the obtained resin substrate S4, a photochromic lens was obtained in which a photochromic layer was laminated on the resin substrate S4 in the same manner as in Example 1-1. The photochromic lenses (molded samples) thus obtained were subjected to the evaluation and measurement described above in (1). The results are shown in Tables 1 to 4.

[0127] [Examples 5 to 25, Comparative Examples 1 to 5] A laminated lens (a photochromic lens having a photochromic layer laminated thereon) was produced in the same manner as in Example 1, except that the resin base material (resin substrate), components, additive amounts, and thickness were changed as shown in Table 1. The obtained photochromic lenses (molded samples) were subjected to the evaluation and measurement described above in (1). The evaluation results are shown in Tables 1 to 4.

[0128] [Table 1]

[0129] [Table 2]

[0130] [Table 3]

[0131] [Table 4]

[0132] This application claims priority based on Japanese Patent Application No. 2021-046914, filed on March 22, 2021, the disclosure of which is incorporated herein in its entirety. [Explanation of symbols]

[0133] 10 Injection molding equipment 12 PCB 12a surface (curved surface) 14, 15 Resin substrate 14a, 15a surfaces (curved surfaces) 16 Fixing member 18 Injection part 20 gap 22 Space 23 Space 24 Notch 30 Laminated lens (laminate) 32 Photochromic layer 32a Surface (objective surface) 34 Protrusion 36 Resin substrate 36a Surface (eye surface) i Width in the thickness direction of the space 22 ii. Diameter width of space 22 iii) Diameter of resin substrate 36 a, b radius of curvature c, d Width in the thickness direction of the resin substrate

Claims

1. A substantially circular substrate; a substantially circular resin substrate disposed opposite the surface of the substrate; a fixing member for fixing a peripheral edge of the substrate and a peripheral edge of the resin substrate; a gap formed between the substrate and the resin substrate, the gap having a width in the thickness direction of the substantially circular center of the substrate of 0.1 to 0.7 mm; an injection portion provided in the fixing member for injecting a polymerizable composition into the gap; a space formed on at least a portion of the periphery of the gap, the space communicating with the injection portion and the gap; a method for manufacturing a photochromic lens using an injection molding device, wherein the space is formed in at least a part of a periphery of the resin substrate, and a width of the space in a thickness direction is larger than a width of the gap in the thickness direction, injecting the polymerizable composition from the injection portion and filling the gap with the polymerizable composition through the space; a step of heating the filled polymerizable composition to polymerize and harden it, thereby forming a photochromic layer on the resin substrate; removing the obtained laminate composed of the resin substrate and the photochromic layer; Including, The thickness of the approximately circular center of the photochromic layer is 0.1 mm to 0.7 mm, The method for producing a photochromic lens, wherein the polymerizable composition contains an isocyanate compound, a thiol compound, a polyol compound, and a photochromic compound, and contains the photochromic compound in an amount of 1,000 ppm to 8,000 ppm.

2. The method for producing a photochromic lens according to claim 1 , wherein the photochromic compound is a naphthopyran-based compound.

3. The method for producing a photochromic lens according to claim 1 or 2, wherein the polyol compound is a compound represented by the following general formula (iia): 【Chemistry 10】 (In general formula (iia), R １ and R ２ represents a hydrogen atom or an alkyl group having 1 to 18 carbon atoms, and at least one of them is a hydrogen atom. １ may be the same or different, and multiple R ２ may be the same or different, and m represents an integer of 15 or more and 500 or less.

4. The method for manufacturing a photochromic lens according to any one of claims 1 to 3, wherein the resin substrate contains a thiourethane resin.

5. The method for producing a photochromic lens according to any one of claims 1 to 4, wherein the viscosity (25°C) of the polymerizable composition is 5 to 1000 mPa·s.

6. After the step of removing the laminate, 6. A method for manufacturing a photochromic lens according to claim 1, comprising the steps of removing the polymerizable composition that has been polymerized and cured in the space around the periphery of the laminate, and exposing the photochromic layer obtained by polymerization and curing in the gap at an end face of the laminate.

7. A photochromic layer having an objective surface and a resin substrate laminated on the photochromic layer, the photochromic layer is made of a polymerized and cured product of a polymerizable composition containing an isocyanate compound, a thiol compound, a polyol compound, and a photochromic compound, and contains 1,000 ppm to 8,000 ppm of the photochromic compound; the thickness of the approximately circular center of the photochromic layer is 0.1 mm to 0.7 mm; A photochromic lens having a protrusion on at least a part of the periphery of the photochromic layer, the protrusion having a thickness greater than the thickness of a portion surrounded by the periphery.

8. 8. The photochromic lens according to claim 7, wherein the four-point average thickness of the peripheral edge of the photochromic layer is 0.1 to 2.5 mm.

9. 9. The photochromic lens according to claim 7, wherein the difference between the four-point average thickness of the peripheral edge of the photochromic layer and the thickness of the approximately circular center of the photochromic layer is 0.3 mm or less.

10. The photochromic lens according to any one of claims 7 to 9, wherein the initial luminous transmittance of the photochromic lens is 80% or more.

11. The photochromic lens according to any one of claims 7 to 10, wherein the photochromic layer including the objective surface is in contact with the resin substrate.

12. The photochromic lens according to any one of claims 7 to 11, wherein the photochromic compound is a naphthopyran-based compound.

13. The photochromic lens according to any one of claims 7 to 12, wherein the polyol compound is a compound represented by the following general formula (iia): 【Chemistry 11】 (In general formula (iia), R １ and R ２ represents a hydrogen atom or an alkyl group having 1 to 18 carbon atoms, and at least one of them is a hydrogen atom. １ may be the same or different, and multiple R ２ may be the same or different, and m represents an integer of 15 or more and 500 or less.

14. The photochromic lens according to any one of claims 7 to 13, wherein the resin substrate comprises a polythiourethane resin.

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