WO2017175407A1 - Procédé de production d'un élément optique - Google Patents

Procédé de production d'un élément optique Download PDF

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Publication number
WO2017175407A1
WO2017175407A1 PCT/JP2016/076848 JP2016076848W WO2017175407A1 WO 2017175407 A1 WO2017175407 A1 WO 2017175407A1 JP 2016076848 W JP2016076848 W JP 2016076848W WO 2017175407 A1 WO2017175407 A1 WO 2017175407A1
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Prior art keywords
compound
mixture
optical member
bis
mol
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PCT/JP2016/076848
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English (en)
Japanese (ja)
Inventor
幸夫 影山
上坂　昌久
山本　明典
Original Assignee
ホヤ レンズ タイランド リミテッド
幸夫 影山
上坂　昌久
山本　明典
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Application filed by ホヤ レンズ タイランド リミテッド, 幸夫 影山, 上坂　昌久, 山本　明典 filed Critical ホヤ レンズ タイランド リミテッド
Priority to JP2016568453A priority Critical patent/JPWO2017175407A1/ja
Publication of WO2017175407A1 publication Critical patent/WO2017175407A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • G—PHYSICS
    • G02—OPTICS
    • G02C—SPECTACLES; SUNGLASSES OR GOGGLES INSOFAR AS THEY HAVE THE SAME FEATURES AS SPECTACLES; CONTACT LENSES
    • G02C7/00—Optical parts

Definitions

  • the present invention relates to a method for producing an optical member and a method for producing a polythiol mixture.
  • Patent Document 1 describes a method of manufacturing a plastic lens that can stabilize the dyeability of a thiourethane plastic lens.
  • a plastic lens manufacturing method for manufacturing a plastic lens from a polymer obtained by polymerizing a thiol compound containing a thiol group and an isocyanate compound containing an isocyanate group the thiol group and the isocyanate group are predetermined.
  • a method for producing a plastic lens characterized in that a thiol compound and an isocyanate compound are used so that the fluctuation of the functional group molar ratio falls within a predetermined range. .
  • Patent Document 1 states that stabilization of the dyeability of a plastic lens is an issue, and it is described that the dispersion of the dyeability has a great influence on the thiol equivalent representing the purity of the raw material thiol compound, but the heat resistance is evaluated. It has not been.
  • An object of one embodiment of the present invention is to provide a method for producing an optical member from which an optical member having excellent heat resistance is obtained, and a method for producing a polythiol mixture.
  • the inventor When using a mixture of specific thiol compounds as the monomer of the polymerization composition, the inventor obtains an optical member having excellent heat resistance by setting the measured value of the thiol equivalent of the mixture within a predetermined range. I found out that
  • Step 1 A step of mixing a mixture 1 of the following compound 1-1, the following compound 1-2 and the following compound 1-3 with a polyiso (thio) cyanate compound to obtain a polymerization composition
  • Step 2 a step of polymerizing the polymerization composition obtained in Step 1 to obtain an optical member
  • It is a manufacturing method of the optical member whose measured value of the thiol equivalent of the mixture 1 of the process 1 is 102 g / eq or less.
  • Step A 2-Mercaptoethanol and epichlorohydrin are reacted in the presence of an amine catalyst to obtain a compound represented by the formula (1): Obtaining a compound represented by: Step B: By reacting the compound obtained in Step A with sodium sulfide, the formula (2): Obtaining a compound represented by: Step C: reacting the compound obtained in Step B with thiourea in the presence of a mineral acid to obtain an isothiuronium salt; Step D: a step of hydrolyzing the isothiuronium salt obtained in Step C with a basic substance to obtain a mixture of Compound 1-1, Compound 1-2, and Compound 1-3; Step E: washing the mixture obtained in Step D with mineral acid and water and purifying the mixture, It is a manufacturing method of the polythiol mixture which makes the measured value of the thiol equivalent of the mixture obtained at the process E below 102 g / eq.
  • Step 1 Mixture 1 of Compound 1-1, Compound 1-2 and Compound 1-3 (hereinafter also referred to as “polythiol mixture” or “mixture 1”) and a polyiso (thio) cyanate compound are mixed to form a polymerization composition.
  • Obtaining Step 2 a step of polymerizing the polymerization composition obtained in Step 1 to obtain an optical member; With The measured value of the thiol equivalent of the mixture 1 in step 1 is 102 g / eq or less.
  • Tg of the optical member obtained can be raised by using the mixture of the measured value of the thiol equivalent of the above-mentioned range, and the optical member which has the outstanding heat resistance is obtained.
  • the polythiol mixture includes the following compound 1-1, the following compound 1-2, and the following compound 1-3.
  • the measured value of the thiol equivalent of the polythiol mixture is 102 g / eq or less, preferably 100 g / eq or less, more preferably 99 g / eq or less.
  • the measured value of the thiol equivalent of the polythiol mixture is preferably 95 g / eq or more, more preferably 96 g / eq or more, still more preferably 97 g / eq or more, and further preferably 98 g / eq or more in order to obtain excellent heat resistance. In this range, in addition to excellent heat resistance, there are also effects of suppressing striae and cloudiness.
  • a thiol equivalent means the mass (g) per unit quantity (eq) of the mercapto group contained in a polythiol mixture.
  • the measuring method of the measured value of thiol equivalent is based on the method described in the Examples.
  • the polythiol mixture is not particularly limited, but is preferably obtained by a production method including the following steps A to E for adjustment of the measured value of the thiol equivalent.
  • step A 2-mercaptoethanol and epichlorohydrin are reacted in the presence of an amine catalyst to obtain the formula (1): To obtain a compound represented by:
  • the molar ratio of 2-mercaptoethanol to epichlorohydrin is preferably 60/40 to 40/60, more preferably 60/40 to 50/50, and still more preferably 55/45 to 50/50.
  • amine catalyst examples include triethylamine, trimethylamine, tripropylamine, and the like.
  • the compounding amount of the amine catalyst is preferably 0.1 to 10 parts by mass, more preferably 0.3 to 7 parts by mass, and further preferably 0 to 100 parts by mass of the total of 2-mercaptoethanol and epichlorohydrin. .5 to 5 parts by mass.
  • the reaction temperature is preferably 0 to 60 ° C., more preferably 10 to 55 ° C., and still more preferably 20 to 50 ° C.
  • the reaction time is, for example, 30 minutes to 2 hours.
  • step B the compound obtained in step A is reacted with sodium sulfide to give the formula (2): To obtain a compound represented by:
  • the amount of sodium sulfide used is preferably more than 50.0 mol%, more preferably, in order to adjust the measured value of thiol equivalent and obtain excellent heat resistance with respect to 100 mol% of the compound obtained in Step A. 51.0 mol% or more, more preferably 52.0 mol% or more.
  • the amount of sodium sulfide used is preferably 55.0 mol% or less, more preferably, in order to adjust the measured value of the thiol equivalent with respect to 100 mol% of the compound obtained in Step A and to obtain excellent heat resistance. It is 54.0 mol% or less, More preferably, it is 53.0 mol% or less, More preferably, it is 52.0 mol% or less, More preferably, it is 51.5 mol% or less.
  • Sodium sulfide is preferably added as an aqueous solution.
  • concentration of the aqueous sodium sulfide solution is preferably 40 to 80% by mass, more preferably 45 to 70% by mass, and further preferably 50 to 60% by mass.
  • the reaction temperature is preferably 0 to 60 ° C., more preferably 10 to 55 ° C., and still more preferably 20 to 50 ° C.
  • the reaction time is, for example, about 30 minutes to 2 hours.
  • Step C the compound obtained in Step B is reacted with thiourea in the presence of a mineral acid to obtain an isothiuronium salt.
  • the mineral acid include hydrochloric acid, nitric acid, sulfuric acid and the like.
  • the mineral acid is preferably added as an aqueous solution.
  • the concentration of the mineral acid aqueous solution is preferably 10 to 50% by mass, more preferably 20 to 45% by mass, and further preferably 30 to 40% by mass.
  • the blending amount of the mineral acid is preferably 100 to 300 mol%, more preferably 110 to 200 mol%, still more preferably with respect to 100 mol% of the total blending amount of 2-mercaptoethanol and epichlorohydrin in Step A. Is 130 to 180 mol%.
  • the reaction temperature is preferably 80 to 130 ° C, more preferably 90 to 120 ° C, and still more preferably 100 to 115 ° C.
  • the reaction time is, for example, about 5 to 15 hours.
  • Step D the isothiuronium salt obtained in Step C is hydrolyzed with a basic substance to obtain a mixture of Compound 1-1, Compound 1-2, and Compound 1-3.
  • the basic substance include sodium hydroxide and potassium hydroxide, and sodium hydroxide is preferable.
  • the basic substance is preferably added as an aqueous solution. In this case, the concentration of the basic substance aqueous solution is preferably 10 to 50% by mass, more preferably 20 to 45% by mass, and still more preferably 25 to 45% by mass. is there.
  • the reaction temperature is preferably 40 to 100 ° C, more preferably 50 to 90 ° C, and still more preferably 55 to 80 ° C.
  • the reaction time is, for example, about 1 to 8 hours.
  • step E the mixture obtained in step D is washed with mineral acid and water to purify the mixture.
  • Suitable examples of the mineral acid are the same as those exemplified in Step C. Washing with water is carried out by a conventional method. In addition, you may remove the organic solvent used by washing
  • the mixture obtained in step E is preferably used as mixture 1 in step 1.
  • the polyiso (thio) cyanate compound means at least one selected from a polyisocyanate compound and a polyisothiocyanate compound.
  • the polyiso (thio) cyanate compound is preferably a polyisocyanate compound.
  • Examples of the polyiso (thio) cyanate compound include a polyiso (thio) cyanate compound having one or more aromatic rings, an alicyclic polyiso (thio) cyanate compound, and a linear or branched aliphatic polyiso (thio) cyanate compound. Can be mentioned.
  • polyiso (thio) cyanate compound having one or more aromatic rings examples include diisocyanatobenzene, 2,4-diisocyanatotoluene, ethylphenylene diisocyanate, isopropylphenylene diisocyanate, dimethylphenylene diisocyanate, diethylphenylene diisocyanate, diisopropylphenylene.
  • Examples of alicyclic polyiso (thio) cyanate compounds include diisocyanatocyclohexane, bis (isocyanatomethyl) cyclohexane, bis (isocyanatocyclohexyl) methane, bis (isocyanatomethyl) bicycloheptane, 2,5-diisocyanato-1, 4-dithiane, 2,5-bis (isocyanatomethyl) -1,4-dithiane, 4,5-diisocyanato-1,3-dithiolane, 4,5-bis (isocyanatomethyl) -1,3-dithiolane, Examples include 4,5-bis (isocyanatomethyl) -2-methyl-1,3-dithiolane.
  • linear or branched aliphatic polyiso (thio) cyanate compounds include hexamethylene diisocyanate, 2,2-dimethylpentane diisocyanate, 2,2,4-trimethylhexane diisocyanate, butene diisocyanate, and 1,3-butadiene-1.
  • the polyiso (thio) cyanate compound is preferably selected from xylylene diisocyanate, bis (isocyanatomethyl) cyclohexane, bis (isocyanatocyclohexyl) methane, and bis (isocyanatomethyl) bicycloheptane in order to improve heat resistance. At least one.
  • the mixing ratio of the polyiso (thio) cyanate compound and the polythiol mixture is such that the molar ratio of iso (thio) cyanate group / mercapto group is usually 0.5 to 2.0, preferably 0.95 to 1.05. is there.
  • Step 1 in addition to a polyiso (thio) cyanate compound and a polythiol mixture, a polymerization catalyst such as organic tin such as dimethyltin dichloride, a release agent such as butoxyethyl acid phosphate, an antioxidant, an ultraviolet stabilizer, and coloring prevention You may mix
  • a polymerization composition can be obtained by mixing the above-mentioned various components by a usual method.
  • step 2 the polymerization composition obtained in step 1 is polymerized to obtain an optical member.
  • the optical member is a spectacle lens
  • the polymerization is preferably a cast polymerization method.
  • the spectacle lens can be obtained, for example, by performing polymerization by injecting a polymerization composition into a mold die in which a glass or metal mold and a tape or gasket are combined.
  • the polymerization conditions can be appropriately set according to the polymerization composition.
  • the polymerization initiation temperature is usually 0 to 50 ° C., preferably 20 to 40 ° C. It is preferable to raise the temperature from the polymerization start temperature and then heat to form a cured film. For example, the temperature rise is usually 110 to 130 ° C.
  • the spectacle lens may be released and an annealing process may be performed.
  • the temperature of the annealing treatment is preferably 100 to 150 ° C.
  • optical member An example of the optical member is a spectacle lens.
  • the surface shape of the spectacle lens is not particularly limited, and may be any of a flat surface, a convex surface, a concave surface, and the like.
  • the spectacle lens may be any of a single focus lens, a multifocal lens, a progressive power lens, and the like.
  • a progressive-power lens normally, the near portion region (near portion) and the progressive portion region (intermediate region) are included in the lower region, and the far portion region (distance portion) is the upper portion. Included in the region.
  • the spectacle lens may be a finish spectacle lens or a semi-finish spectacle lens.
  • the thickness and diameter of the spectacle lens are not particularly limited, but the thickness is usually about 1 to 30 mm and the diameter is usually about 50 to 100 mm.
  • the refractive index ne of the spectacle lens is preferably 1.53 or more, more preferably 1.55 or more, more preferably 1.58 or more, still more preferably 1.60 or more, still more preferably 1.67 or more, still more preferably. 1.70 or more, preferably 1.80 or less.
  • Tg glass transition temperature
  • the test resin was observed under a fluorescent lamp in a dark box and judged according to the following criteria.
  • Example 1 (Synthesis of polythiol mixture) 92.5 g (1.000 mol) of epichlorohydrin was added dropwise to a mixed solution of 78.1 g (1.000 mol) of 2-mercaptoethanol and 2.0 g of triethylamine over 1 hour while maintaining the internal temperature at 35 to 40 ° C. Aging was performed at 40 ° C. for 1 hour (step A). An aqueous solution in which 125.0 g (0.520 mol) of sodium sulfide nonahydrate was previously dissolved in 100 g of pure water was added dropwise to this reaction solution over 1 hour while maintaining the internal temperature at 40 to 45 ° C., and further at 45 ° C. for 1 hour. Aging was performed (step B).
  • Step C 303.8 g (3.0 mol) of 36 mass% hydrochloric acid aqueous solution and 190.3 g (2.50 mol) of thiourea were added to the reaction solution, and the mixture was heated and stirred at 110 ° C. for 9 hours (Step C).
  • 400 mL of toluene was added, 600.4 g (4.5 mol) of a 30% by mass aqueous sodium hydroxide solution was gradually added, and hydrolysis was performed at 60 ° C. for 4 hours (Step D).
  • 130 mL of 36 mass% hydrochloric acid aqueous solution was added, and washing was performed at 40 ° C for 1 hour. Subsequently, it was washed twice with 100 mL of water, the organic layer was recovered, and toluene was removed with a rotary evaporator to obtain a target polythiol mixture (Step E).
  • the measured value of the thiol equivalent of the polythiol mixture was 98 g / eq.
  • This polymerized composition was defoamed at 200 Pa for 1 hour, and then filtered through a PTFE (polytetrafluoroethylene, filtration accuracy: 5.0 ⁇ m) filter.
  • the mixture was poured into a lens mold composed of a glass mold having a diameter of 75 mm and ⁇ 4.00 D and a tape.
  • the mold was removed from the electric furnace and released to obtain a spectacle lens.
  • the obtained spectacle lens was further annealed at 120 ° C. for 3 hours.
  • the obtained polymer had a heat resistance (Tg) of 103 ° C.
  • striae and cloudiness were evaluated. The results are summarized in Table 1.
  • Example 2 the amount of sodium sulfide nonahydrate used is 0.515 mol, in Example 3, the amount of sodium sulfide nonahydrate used is 0.510 mol, and in Comparative Example 1, the amount of sodium sulfide nonahydrate used is In 0.500 mol, in Comparative Example 2, the amount of sodium sulfide nonahydrate was changed to 0.490 mol, and polymerization was performed in the same manner as in Example 1 except that polythiol mixtures having different thiol equivalents were used. Prepared and measured heat resistance. Furthermore, striae and cloudiness were evaluated. The results are summarized in Table 1. In addition, the thiol equivalent in a table
  • surface is a measured value.
  • Examples 4-6 Polymerization was carried out in the same manner as in Example 3 except that the type and amount of the polyisocyanate compound and the amount of polythiol were changed as shown in Table 2, and the heat resistance was measured. Furthermore, striae and cloudiness were evaluated. The results are summarized in Table 2. In addition, the thiol equivalent in a table
  • surface is a measured value.
  • Comparative Examples 3-5 Polymerization was performed in the same manner as in Comparative Example 1 except that the type and amount of the polyisocyanate compound and the amount of polythiol were changed as shown in Table 2, and the heat resistance was measured. Furthermore, striae and cloudiness were evaluated. The results are summarized in Table 2. In addition, the thiol equivalent in a table
  • surface is a measured value.
  • Step 1 A step of mixing a mixture 1 of the following compound 1-1, the following compound 1-2 and the following compound 1-3 with a polyiso (thio) cyanate compound to obtain a polymerization composition
  • Step 2 a step of polymerizing the polymerization composition obtained in Step 1 to obtain an optical member
  • It is a manufacturing method of the optical member whose measured value of the thiol equivalent of the mixture 1 of the process 1 is 102 g / eq or less.
  • the Tg of the obtained optical member can be increased, and an optical member having excellent heat resistance can be obtained.
  • Step A 2-Mercaptoethanol and epichlorohydrin are reacted in the presence of an amine catalyst to obtain a compound represented by the formula (1): Obtaining a compound represented by: Step B: By reacting the compound obtained in Step A with sodium sulfide, the formula (2): Obtaining a compound represented by: Step C: reacting the compound obtained in Step B with thiourea in the presence of a mineral acid to obtain an isothiuronium salt; Step D: a step of hydrolyzing the isothiuronium salt obtained in Step C with a basic substance to obtain a mixture of Compound 1-1, Compound 1-2, and Compound 1-3; Step E: washing the mixture obtained in Step D with mineral acid and water and purifying the mixture, It is a manufacturing method of the polythiol mixture which makes the measured value of the thiol equivalent of the mixture obtained at the process E below 102 g / eq.
  • the manufacturing method of one embodiment when it is used for manufacturing an optical member by using a mixture of thiol equivalents in the above range, the Tg of the obtained optical member can be increased, and excellent heat resistance can be obtained.

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Physics & Mathematics (AREA)
  • Ophthalmology & Optometry (AREA)
  • General Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Medicinal Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Polyurethanes Or Polyureas (AREA)
  • Eyeglasses (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

La présente invention concerne un procédé de production d'un élément optique grâce auquel un élément optique présentant une excellente résistance à la chaleur peut être obtenu et décrit un procédé de production d'un mélange de polythiol. Le procédé de production d'un élément optique comprend : une étape 1 d'obtention d'une composition polymérisable en mélangeant un mélange 1 contenant un composé 1-1, un composé 1-2, et un composé 1-3 et un composé polyiso(thio)cyanate ; et une étape 2 d'obtention d'un élément optique par polymérisation de la composition polymérisable obtenue dans l'étape 1, la valeur mesurée de la quantité d'équivalent thiol du mélange 1 dans l'étape 1 étant de 102 g/éq. ou moins.
PCT/JP2016/076848 2016-04-06 2016-09-12 Procédé de production d'un élément optique WO2017175407A1 (fr)

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPWO2019189787A1 (ja) * 2018-03-30 2021-02-12 三井化学株式会社 有機メルカプト化合物又はその中間体の製造方法、（ポリ）チオール成分、光学材料用重合性組成物、成形体、光学材料及びレンズ
CN112430326A (zh) * 2020-11-27 2021-03-02 山东益丰生化环保股份有限公司 一种聚硫醇化合物、其制备方法及应用

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JPH07252207A (ja) * 1994-01-26 1995-10-03 Mitsui Toatsu Chem Inc 新規なポリチオール及びそれを用いた含硫ウレタン系プラスチックレンズ
JPH0952931A (ja) * 1995-08-14 1997-02-25 Mitsui Toatsu Chem Inc 新規なポリチオールを用いた含硫ウレタン系プラスチックレンズ
JPH09194558A (ja) * 1996-01-23 1997-07-29 Mitsui Toatsu Chem Inc 含硫ウレタン系プラスチックレンズ
WO2014027428A1 (fr) * 2012-08-14 2014-02-20 三井化学株式会社 Procédé de fabrication pour un composé polythiol, composition polymérisable pour une matière optique et son utilisation
WO2014203812A1 (fr) * 2013-06-18 2014-12-24 三菱瓦斯化学株式会社 Composition pour matériau optique
JP2015520765A (ja) * 2012-05-23 2015-07-23 ケイオーシーソリューション カンパニー リミテッドＫｏｃ Ｓｏｌｕｔｉｏｎ Ｃｏ．， Ｌｔｄ． 新規のポリチオール化合物の製造方法及びこれを含む光学材料用重合性組成物

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JPH07252207A (ja) * 1994-01-26 1995-10-03 Mitsui Toatsu Chem Inc 新規なポリチオール及びそれを用いた含硫ウレタン系プラスチックレンズ
JPH0952931A (ja) * 1995-08-14 1997-02-25 Mitsui Toatsu Chem Inc 新規なポリチオールを用いた含硫ウレタン系プラスチックレンズ
JPH09194558A (ja) * 1996-01-23 1997-07-29 Mitsui Toatsu Chem Inc 含硫ウレタン系プラスチックレンズ
JP2015520765A (ja) * 2012-05-23 2015-07-23 ケイオーシーソリューション カンパニー リミテッドＫｏｃ Ｓｏｌｕｔｉｏｎ Ｃｏ．， Ｌｔｄ． 新規のポリチオール化合物の製造方法及びこれを含む光学材料用重合性組成物
WO2014027428A1 (fr) * 2012-08-14 2014-02-20 三井化学株式会社 Procédé de fabrication pour un composé polythiol, composition polymérisable pour une matière optique et son utilisation
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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPWO2019189787A1 (ja) * 2018-03-30 2021-02-12 三井化学株式会社 有機メルカプト化合物又はその中間体の製造方法、（ポリ）チオール成分、光学材料用重合性組成物、成形体、光学材料及びレンズ
JP7168656B2 (ja) 2018-03-30 2022-11-09 三井化学株式会社 有機メルカプト化合物又はその中間体の製造方法、組成物、光学材料用重合性組成物、成形体、光学材料及びレンズ
CN112430326A (zh) * 2020-11-27 2021-03-02 山东益丰生化环保股份有限公司 一种聚硫醇化合物、其制备方法及应用

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