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WO2013002409A1 - Lentille en plastique - Google Patents

Lentille en plastique Download PDF

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Publication number
WO2013002409A1
WO2013002409A1 PCT/JP2012/066894 JP2012066894W WO2013002409A1 WO 2013002409 A1 WO2013002409 A1 WO 2013002409A1 JP 2012066894 W JP2012066894 W JP 2012066894W WO 2013002409 A1 WO2013002409 A1 WO 2013002409A1
Authority
WO
WIPO (PCT)
Prior art keywords
plastic lens
lens
bis
compound represented
formula
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/JP2012/066894
Other languages
English (en)
Japanese (ja)
Inventor
伸介 伊藤
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Hoya Corp
Original Assignee
Hoya Corp
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Hoya Corp filed Critical Hoya Corp
Priority to KR1020137034670A priority Critical patent/KR20140045453A/ko
Priority to CN201280032479.6A priority patent/CN103649821B/zh
Publication of WO2013002409A1 publication Critical patent/WO2013002409A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
    • G02B1/04—Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of organic materials, e.g. plastics
    • G02B1/041—Lenses
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/34—Heterocyclic compounds having nitrogen in the ring
    • C08K5/3442—Heterocyclic compounds having nitrogen in the ring having two nitrogen atoms in the ring
    • C08K5/3462—Six-membered rings
    • C08K5/3465—Six-membered rings condensed with carbocyclic rings
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P13/00—Preparation of nitrogen-containing organic compounds
    • C12P13/02—Amides, e.g. chloramphenicol or polyamides; Imides or polyimides; Urethanes, i.e. compounds comprising N-C=O structural element or polyurethanes
    • G—PHYSICS
    • G02—OPTICS
    • G02C—SPECTACLES; SUNGLASSES OR GOGGLES INSOFAR AS THEY HAVE THE SAME FEATURES AS SPECTACLES; CONTACT LENSES
    • G02C7/00—Optical parts
    • G02C7/02—Lenses; Lens systems ; Methods of designing lenses

Definitions

  • the present invention relates to a plastic lens. More specifically, the present invention relates to a plastic lens that is almost colorless and suitable for use as a spectacle lens.
  • Plastic lenses made of optical resins having excellent transparency are used in a wide range of fields in place of inorganic glass lenses due to their advantages such as light weight and excellent workability, and are particularly suitable as spectacle lenses.
  • the spectacle lens is required to have an ultraviolet absorbing ability in order to protect the eyes from harmful ultraviolet rays, and an ultraviolet absorber may be added when manufacturing a spectacle lens made of a plastic material.
  • an ultraviolet absorber may be added when manufacturing a spectacle lens made of a plastic material.
  • the plastic lens itself is yellowed by adding an ultraviolet absorber.
  • yellowing of a plastic lens also occurs through a manufacturing process such as heat treatment, and various studies have been made to eliminate such yellowing of a plastic lens.
  • Patent Document 1 discloses a method for manufacturing a lens in which an anthraquinone compound having a specific structure as a blue dye is added to a urethane-based resin.
  • the method is a method for manufacturing a lens limited to a urethane-based resin. The transparency of the resulting lens was not satisfactory depending on the application.
  • An object of the present invention is to provide a plastic lens that is almost colorless and transparent without being yellowed even if it is manufactured through a process such as addition of an ultraviolet absorber or heat treatment.
  • the inventor of the present invention contains an anthraquinone compound having a specific structure, and even when manufactured through a process such as addition of an ultraviolet absorber or heat treatment, it is extremely yellow.
  • the present invention has been completed by finding out that it can be a plastic lens that is nearly colorless and transparent. That is, this invention is a plastic lens characterized by including the compound represented by following formula (1).
  • R 1 , R 2 and R 3 each independently represents a group selected from a hydrogen atom or an alkyl group having 1 to 8 carbon atoms.
  • the plastic lens of the present invention containing an anthraquinone compound having a specific structure is a plastic lens that is almost colorless and transparent without being yellowed even if it is manufactured through a process such as addition of an ultraviolet absorber or heat treatment. .
  • the plastic lens of the present invention includes an anthraquinone compound represented by the following formula (1).
  • R 1 , R 2 and R 3 each independently represents a group selected from a hydrogen atom or an alkyl group having 1 to 8 carbon atoms, and the preferred alkyl group has 1 to 3 carbon atoms.
  • the alkyl group having 1 to 8 carbon atoms may be any of linear, branched and cyclic, such as methyl group, ethyl group, propyl group, isopropyl group, n-butyl group, s-butyl group.
  • a methyl group and an ethyl group are preferable.
  • Examples of the compound represented by the above formula (1) that can be preferably used in the present invention include 1,4-bis [(2,6-dimethylphenyl) amino] anthracene-9,10-dione, 1,4 -Bis [(2,6-diethylphenyl) amino] anthracene-9,10-dione, 1,4-bis [(2,6-dipropylphenyl) amino] anthracene-9,10-dione, 1,4- Bis [(2,6-dimethyl-4-methylphenyl) amino] anthracene-9,10-dione, 1,4-bis [(2,6-diethyl-4-methylphenyl) amino] anthracene-9,10- Dione, 1,4-bis [(2,6-dipropyl-4-methylphenyl) amino] anthracene-9,10-dione, 1,4-bis [(2,6-dimethyl-4-ethylphen Nyl) amino] anthracene-9,
  • the content of the anthraquinone compound represented by the above formula (1) contained in the plastic lens depends on the type of monomer used as a raw material for the plastic lens and the type of additive added as necessary. Although it may be determined as appropriate, it is preferably 0.001 to 1000 ppm by mass, more preferably 0.01 to 100 ppm by mass, and still more preferably 0.1 to 10 ppm by mass with respect to the total amount of monomers. If the said content is 0.001 mass ppm or more, the effect which suppresses the yellowness of a plastic lens can be exhibited, and if it is 1000 mass ppm or less, sufficient transparency of a plastic lens can be ensured.
  • the plastic lens of the present invention can be produced by mixing and adding an anthraquinone compound represented by the above formula (1) with various raw material monomers, and an anthraquinone compound represented by the above formula (1).
  • the compound can also be produced by adsorbing and penetrating the surface of the plastic lens later.
  • the plastic applied to the plastic lens of the present invention is not particularly limited and may be those usually used for resin lenses.
  • resin lenses For example, urethane resin, thiourethane resin, polycarbonate resin, polystyrene resin, polyacrylate Examples thereof include resins and melamine resins.
  • urethane resins and thiourethane resins which are excellent in transparency and impact resistance and are suitable for use in spectacle lenses, are preferable.
  • a urethane resin or a thiourethane resin when applied as a plastic, for example, monomers such as a polyisocyanate compound, a polythiol compound, and a polyol compound, and an ultraviolet absorber, a polymerization catalyst, if necessary.
  • monomers such as a polyisocyanate compound, a polythiol compound, and a polyol compound, and an ultraviolet absorber, a polymerization catalyst, if necessary.
  • Additives such as antioxidants and mold release agents can be used, and the monomers and additives can be used alone or in combination of two or more. Examples of the monomer and additive include the following.
  • an aromatic polyisocyanate compound an aromatic polyisocyanate compound, an aliphatic or alicyclic polyisocyanate compound and the like can be used, and among them, an aromatic polyisocyanate compound is preferably used.
  • aromatic polyisocyanate compounds include 1,3-phenylene diisocyanate, 1,4-phenylene diisocyanate, 2,4-tolylene diisocyanate, 2,6-tolylene diisocyanate, o-xylylene diisocyanate, and m-xylylene diisocyanate.
  • Examples of the aliphatic polyisocyanate compound include 1,6-hexamethylene diisocyanate, lysine ester triisocyanate, mesitylene triisocyanate, 1,3,6-hexamethylene triisocyanate, and examples of the alicyclic polyisocyanate compound.
  • isophorone diisocyanate dicyclohexylmethane diisocyanate, 1,3-cyclohexane diisocyanate, 1,4-cyclohexane diisocyanate, 1,2-bis (isocyanatomethyl) cyclohexane, 1,3-bis (isocyanatomethyl) cyclohexane, 1, 4-bis (isocyanatomethyl) cyclohexane, 2,5-bis (isocyanatomethyl) bicyclo- [2,2,1] -heptane, 2,6-bis (isocyanatomethyl) bi Black - [2,2,1] - heptane, 1,3,5-tris (isocyanatomethyl) cyclohexane, bicycloheptane triisocyanate.
  • These aliphatic and alicyclic polyisocyanate compounds may be used alone or in combination of two or more.
  • polythiol compound examples include ethylene glycol bis (2-mercaptoacetate), trimethylolpropane bis (2-mercaptoacetate), pentaerythritol tetrakis (3-mercaptopropionate), trimethylolpropane bis (2-mercaptopropioate).
  • an aliphatic or aromatic polyol compound or the like can be used as the polyol compound.
  • the aliphatic polyol compound include ethylene glycol, diethylene glycol, propylene glycol, dipropylene glycol, butylene glycol, neopentyl glycol, glycerin, trimethylolethane, trimethylolpropane, butanetriol, 1,2-methylglucoside, penta Erythritol, dipentaerythritol, tripentaerythritol, triethylene glycol, polyethylene glycol, tris (2-hydroxyethyl) isocyanurate, cyclobutanediol, cyclopentanediol, cyclohexanediol, cycloheptanediol, cyclooctanediol, bicyclo [4.3 .0] -nonanediol, dicyclohexanedio
  • aromatic polyol compound examples include dihydroxynaphthalene, trihydroxynaphthalene, tetrahydroxynaphthalene, dihydroxybenzene, benzenetriol, trihydroxyphenanthrene, bisphenol A, bisphenol F, xylylene glycol, and tetrabromobisphenol. These aliphatic and alicyclic polyol compounds may be used alone or in combination of two or more.
  • a ultraviolet absorber As an additive added as needed, a ultraviolet absorber, a polymerization catalyst, antioxidant, a mold release agent, etc. can be used.
  • an ultraviolet absorber when an ultraviolet absorber is added in the production of the plastic lens of the present invention, the effect of the present invention due to the inclusion of the anthraquinone compound represented by the above formula (1) is exhibited remarkably.
  • the ultraviolet absorber include 2,4-dihydroxybenzophenone, 2-hydroxy-4-methoxybenzophenone, 2-hydroxy-4-methoxybenzophenone-5-sulphonic acid, 2-hydroxy-4-n-octoxybenzophenone.
  • benzophenone compounds such as 2-hydroxy-4-n-dodecyloxybenzophenone, 2-hydroxy-4-benzyloxybenzophenone and 2,2′-dihydroxy-4-methoxybenzophenone; 2- (2′-hydroxy-5 '-Methylphenyl) benzotriazole, 2- (2'-hydroxy-3', 5'-di-t-butylphenyl) -5-chlorobenzotriazole, 2- (2'-hydroxy-3'-t-butyl) -5'-methylphenyl) -5-chlorobenzotriazole, 2- 2'-hydroxy-3 ', 5'-di-t-amylphenyl) benzotriazole, 2- (2'-hydroxy-3', 5'-di-t-butylphenyl) benzotriazole, 2- (2 '-Hydroxy-5'-t-butylphenyl) benzotriazole, 2- (2'-hydroxy-5'-t-octylphenyl
  • the polymerization catalyst is preferably used for adjusting the reaction rate of monomer polymerization.
  • dibutyltin diacetate, dibutyltin dilaurate, dibutyltin dichloride, dimethyltin dichloride, monomethyltin trichloride, trimethyltin chloride examples thereof include organic tin compounds such as tributyltin chloride, tributyltin fluoride, and dimethyltin dibromide.
  • These polymerization catalysts may be used alone or in combination of two or more.
  • antioxidants examples include 2,6-di-tert-butyl-p-cresol and 1,6-hexanediol-bis [3- (3,5-di-tert-butyl-4-hydroxyphenyl) propionate. ], Phenolic antioxidants such as 2,4-bis- (n-octylthio) -6- (4-hydroxy-3,5-di-tert-butylanilino) -1,3,5-triazine, and the like. The antioxidants may be used alone or in combination of two or more.
  • the release agent examples include isopropyl acid phosphate, butyl acid phosphate, octyl acid phosphate, nonyl acid phosphate, decyl acid phosphate, isodecyl acid phosphate, tridecyl acid phosphate, stearyl acid phosphate, Phosphoric acid monoester compounds such as propylphenyl acid phosphate and butylphenyl acid phosphate; diisopropyl acid phosphate, dibutyl acid phosphate, dioctyl acid phosphate, diisodecyl acid phosphate, bis (tridecyl acid phosphate), distearyl Acid phosphate, dipropyl phenyl acid phosphate, dibutyl phosphate Such as phosphoric acid diester compounds such as sulfonyl acid phosphate and butoxyethyl acid phosphate. These mold release agents may be used independently and may use 2 or more types together.
  • the present invention also provides a method for producing a plastic lens, wherein in the production of a plastic lens obtained by polymerizing a monomer composition, the compound represented by the above formula (1) is added to the monomer composition for polymerization. .
  • the anthraquinone compound represented by the above formula (1) is added to a monomer composition containing the above-mentioned monomers and additives used as necessary, and this is usually cast polymerization. Can be manufactured.
  • the monomer composition preferably contains an aromatic polyisocyanate compound. There is no restriction
  • the mixture is poured into a mold die in which a glass or metal mold and a resin gasket are combined, and the polymerization is performed by heating.
  • the polymerization temperature and polymerization time are generally about 0.5 to 72 hours at 0 to 150 ° C., although depending on the type of raw material used.
  • the yellowing degree (YI value) of the obtained lens was measured according to the plastic yellowness and yellowing degree test method defined in JIS K7103-1977.
  • Example 1 A 500 ml eggplant-shaped flask was charged with 22.88 g of 4,4′-diphenylmethane diisocyanate and 25.09 g of 1,6-hexamethylene diisocyanate, and JP-506H (trade name, manufactured by Johoku Chemical Co., Ltd.) as a release agent.
  • This mixture was cast into a lens mold having a center thickness of 2 mm through a PTFE membrane filter having a thickness of 1.0 ⁇ m, and polymerized by a temperature program from an initial temperature of 30 ° C. to a final temperature of 120 ° C. over 24 hours to obtain a lens. .
  • the obtained lens was almost yellowish and colorless and transparent, and the YI value was 1.40.
  • Example 2 In Example 1, 1,4-bis [(2,6-diethyl-4-methylphenyl) amino] anthracene-9,10-dione was converted to compound 1,4- A lens was obtained in the same procedure except that bis [(2,4,6-trimethylphenyl) amino] anthracene-9,10-dione was used. The obtained lens was almost yellowish and colorless and transparent, and the YI value was 1.41.
  • Example 1 A lens was obtained in the same manner as in Example 1, except that the compound represented by the formula (1-1) was replaced with the compound represented by the following formula (2). The obtained lens was extremely yellowish and had a YI value of 7.81.
  • Example 4 A lens was obtained in the same manner as in Example 1 except that the anthraquinone compound represented by the formula (1-1) was not blended. The obtained lens was slightly yellowish and had a YI value of 2.1.
  • Example 3 A 500 ml eggplant-shaped flask was charged with 22.25 g of 4,4′-diphenylmethane diisocyanate, 15.74 g of 1,6-hexamethylene diisocyanate and 11.44 g of isophorone diisocyanate, and JP-506H (trade name, Johoku) 0.20 g of Chemical Industry Co., Ltd., 0.06 g of dimethyltin dichloride as a polymerization catalyst, 1.00 g of Seasorb 701 (trade name, manufactured by Sipro Kasei Co., Ltd.) as an ultraviolet absorber, and 2,6 as an antioxidant -1.00 g of di-tert-butyl-p-cresol, compound 1,4-bis [(2,6-diethyl-4-methylphenyl) amino] anthracene-9 represented by the formula (1-1) , 10-dione was added at 0.4 mass ppm, and stirring was continued for 30 minutes under a nitrogen purge at 50 ° C.
  • Example 4 In Example 3, 1,4-bis [(2,6-diethyl-4-methylphenyl) amino] anthracene-9,10-dione was converted into the compound 1,4- A lens was obtained in the same procedure except that bis [(2,4,6-trimethylphenyl) amino] anthracene-9,10-dione was used. The obtained lens was almost yellowish and colorless and transparent, and the YI value was 1.88.
  • Example 8 A lens was obtained in the same manner as in Example 3, except that the anthraquinone compound represented by the formula (1-1) was not blended. The resulting lens was somewhat yellowish and had a YI value of 2.31.
  • the plastic lens containing an anthraquinone compound having a specific structure according to the present invention has a characteristic of being almost colorless and transparent without being yellowed even if it is manufactured through a process such as addition of an ultraviolet absorber or heat treatment. Therefore, it is suitable as an application requiring such characteristics, particularly as a spectacle lens.

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  • Physics & Mathematics (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Ophthalmology & Optometry (AREA)
  • Engineering & Computer Science (AREA)
  • Microbiology (AREA)
  • General Engineering & Computer Science (AREA)
  • Genetics & Genomics (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Biochemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Biotechnology (AREA)
  • Polyurethanes Or Polyureas (AREA)
  • Eyeglasses (AREA)
  • Compositions Of Macromolecular Compounds (AREA)

Abstract

La présente invention concerne une lentille en plastique caractérisée en ce qu'elle contient un composé représenté par la formule (1) [où R1, R2 et R3 sont chacun indépendamment un atome d'hydrogène ou un groupe sélectionné parmi les groupes alkyles comptant 1 à 8 atomes de carbone].
PCT/JP2012/066894 2011-06-30 2012-07-02 Lentille en plastique Ceased WO2013002409A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
KR1020137034670A KR20140045453A (ko) 2011-06-30 2012-07-02 플라스틱 렌즈
CN201280032479.6A CN103649821B (zh) 2011-06-30 2012-07-02 塑料透镜

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2011-146712 2011-06-30
JP2011146712 2011-06-30

Publications (1)

Publication Number Publication Date
WO2013002409A1 true WO2013002409A1 (fr) 2013-01-03

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PCT/JP2012/066894 Ceased WO2013002409A1 (fr) 2011-06-30 2012-07-02 Lentille en plastique

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JP (1) JPWO2013002409A1 (fr)
KR (1) KR20140045453A (fr)
CN (1) CN103649821B (fr)
WO (1) WO2013002409A1 (fr)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2016143898A1 (fr) * 2015-03-12 2016-09-15 ホヤ レンズ タイランド リミテッド Composition d'iso(thio)cyanate, et composition de résine la comprenant pour élément optique
WO2020262659A1 (fr) * 2019-06-28 2020-12-30 ホヤ レンズ タイランド リミテッド Composition polymérisable pour matériaux optiques, matériau optique et procédé de production de matériau optique
US20230305854A1 (en) * 2022-03-25 2023-09-28 Sap Se Reducing downtime during operating system patching

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WO2016174788A1 (fr) * 2015-04-30 2016-11-03 東海光学株式会社 Lentille en matière plastique

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Publication number Priority date Publication date Assignee Title
WO2016143898A1 (fr) * 2015-03-12 2016-09-15 ホヤ レンズ タイランド リミテッド Composition d'iso(thio)cyanate, et composition de résine la comprenant pour élément optique
KR20170117142A (ko) * 2015-03-12 2017-10-20 호야 렌즈 타일랜드 리미티드 이소(티오)시아네이트 조성물 및 그것을 사용한 광학 부재용 수지 조성물
JPWO2016143898A1 (ja) * 2015-03-12 2017-12-21 ホヤ レンズ タイランド リミテッドＨＯＹＡ Ｌｅｎｓ Ｔｈａｉｌａｎｄ Ｌｔｄ イソ（チオ）シアネート組成物及びそれを用いた光学部材用樹脂組成物
EP3269749A4 (fr) * 2015-03-12 2018-10-31 Hoya Lens Thailand Ltd. Composition d'iso(thio)cyanate, et composition de résine la comprenant pour élément optique
US10544283B2 (en) 2015-03-12 2020-01-28 Hoya Lens Thailand Ltd. Iso(thio)cyanate composition, and resin composition including same for optical member
EP3957666A1 (fr) * 2015-03-12 2022-02-23 Hoya Lens Thailand Ltd. Composition d'iso(thio)cyanate et composition de résine pour élément optique la comprenant
US11267953B2 (en) 2015-03-12 2022-03-08 Hoya Lens Thailand Ltd. Iso(thio)cyanate composition, and resin composition including same for optical member
WO2020262659A1 (fr) * 2019-06-28 2020-12-30 ホヤ レンズ タイランド リミテッド Composition polymérisable pour matériaux optiques, matériau optique et procédé de production de matériau optique
US20230305854A1 (en) * 2022-03-25 2023-09-28 Sap Se Reducing downtime during operating system patching
US12014186B2 (en) * 2022-03-25 2024-06-18 Sap Se Reducing downtime during operating system patching

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CN103649821B (zh) 2015-04-01
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KR20140045453A (ko) 2014-04-16

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