WO2023003096A1 - Composition pour lentille à focale variable, lentille à focale variable la comprenant, et son procédé de fabrication - Google Patents

Composition pour lentille à focale variable, lentille à focale variable la comprenant, et son procédé de fabrication Download PDF

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Publication number
WO2023003096A1
WO2023003096A1 PCT/KR2021/017077 KR2021017077W WO2023003096A1 WO 2023003096 A1 WO2023003096 A1 WO 2023003096A1 KR 2021017077 W KR2021017077 W KR 2021017077W WO 2023003096 A1 WO2023003096 A1 WO 2023003096A1
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Prior art keywords
light
polymer resin
variable focus
mixed solution
composition
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PCT/KR2021/017077
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English (en)
Korean (ko)
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배진우
김상연
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한국기술교육대학교 산학협력단
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Publication of WO2023003096A1 publication Critical patent/WO2023003096A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L27/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Compositions of derivatives of such polymers
    • C08L27/02—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Compositions of derivatives of such polymers not modified by chemical after-treatment
    • C08L27/04—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Compositions of derivatives of such polymers not modified by chemical after-treatment containing chlorine atoms
    • C08L27/06—Homopolymers or copolymers of vinyl chloride
    • 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
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
    • C08K5/0016—Plasticisers
    • 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
    • C08K5/04—Oxygen-containing compounds
    • C08K5/10—Esters; Ether-esters
    • C08K5/11—Esters; Ether-esters of acyclic polycarboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L1/00—Compositions of cellulose, modified cellulose or cellulose derivatives
    • C08L1/08—Cellulose derivatives
    • C08L1/10—Esters of organic acids, i.e. acylates
    • C08L1/12—Cellulose acetate
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L101/00—Compositions of unspecified macromolecular compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L31/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an acyloxy radical of a saturated carboxylic acid, of carbonic acid or of a haloformic acid; Compositions of derivatives of such polymers
    • C08L31/02—Homopolymers or copolymers of esters of monocarboxylic acids
    • C08L31/04—Homopolymers or copolymers of vinyl acetate
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L67/00—Compositions of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Compositions of derivatives of such polymers
    • C08L67/02—Polyesters derived from dicarboxylic acids and dihydroxy compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L69/00—Compositions of polycarbonates; Compositions of derivatives of polycarbonates
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B3/00—Simple or compound lenses
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B3/00—Simple or compound lenses
    • G02B3/0006—Arrays
    • G02B3/0012—Arrays characterised by the manufacturing method
    • G02B3/0031—Replication or moulding, e.g. hot embossing, UV-casting, injection moulding
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B3/00—Simple or compound lenses
    • G02B3/12—Fluid-filled or evacuated lenses
    • G02B3/14—Fluid-filled or evacuated lenses of variable focal length

Definitions

  • the present invention relates to a composition for a variable focus lens, a variable focus lens including the same, and a manufacturing method thereof.
  • variable focus lens refers to a lens capable of changing its focal length by changing its external appearance or internal structure by a current, voltage, electric field, or magnetic field provided from the outside.
  • Such a variable focus lens may be in a liquid or gel state, and can be operated with less power than conventional lenses, and can be miniaturized due to a small space required for changing the focus.
  • Korean Patent Publication No. 10-2018-0114382 which is a prior art document, discloses a variable focus lens capable of independently controlling the focal length of both sides by applying a light-transmitting polymer resin and a plasticizer.
  • An object of the present invention is to provide a composition for a variable focus lens capable of improving the ductility of the variable focus lens, a variable focus lens including the composition, and a manufacturing method thereof.
  • a composition for a variable focus lens according to an embodiment of the present invention includes a light-transmitting polymer resin; P(VC-VA) [poly(vinyl chloride-co-vinyl acetate)]; And a plasticizer; includes.
  • the P(VC-VA) may have the following molecular formula 1.
  • a method for manufacturing a variable focus lens according to an embodiment of the present invention includes preparing a mixed solution by dissolving a mixture of a light-transmitting polymer resin, P(VC-VA), and a plasticizer in a solvent; and removing the solvent of the mixed solution.
  • the weight ratio of the light-transmissive polymer resin and P(VC-VA) introduced in the step of preparing the mixed solution may be 1:0.9 to 1:1.1.
  • the content of the DAG introduced in the step of preparing the mixed solution may be 1:1 to 1:11 with respect to the total weight of the light-transmitting polymer resin and P(VC-VA).
  • variable focus lens including the composition for a variable focus lens according to an embodiment of the present invention and a variable focus lens manufactured by the method for manufacturing the same may have higher ductility.
  • FIG. 1(a) shows a variable focus lens according to an embodiment of the present invention
  • FIG. 1(b) is an exploded perspective view of FIG. 1(a).
  • FIG. 2 is a cross-section of the variable focus lens of FIG. 1, illustrating deformation of a lens unit according to supply of power.
  • FIG. 5(a) is a graph measuring the relative permittivity of DBA and Comparative Example 1
  • FIG. 5(b) is a graph measuring the relative permittivity of Examples 1 to 5.
  • Figure 6 (a) is a graph measuring the impedance of DBA and Comparative Example 1
  • Figure 6 (b) is a graph measuring the impedance of Examples 1 to 5.
  • a composition for a variable focus lens includes a light-transmitting polymer resin; P(VC-VA) [poly(vinyl chloride-co-vinyl acetate)]; And a plasticizer; includes.
  • the composition may be provided as a powder or a liquid dissolved in a solvent.
  • P(VC-VA) poly(vinyl chloride-co-vinyl acetate)
  • P(VC-VA) is a polymeric material formed by interconnecting chains of vinyl chloride and vinyl acetate.
  • the P(VC-VA) may be represented by the following molecular formula 1.
  • the molecular weight of the P(VC-VA) may be 100,000 or more in consideration of ductility.
  • P(VC-VA) may be represented by Formula 1 below.
  • the light-transmissive polymer resin is a polymer material having transparency and flexibility, and functions to maintain the shape of a lens and refract an incident wavelength.
  • the light-transmitting polymer resin may be at least one of PVC (Poly vinyl chloride), PC (PolyCarbonate), PET (PolyEthylene Terephthalate), and TAC (TriAcetate Cellulose), and preferably may be PVC that is transparent and easy to process.
  • the light-transmitting polymer resin may have a molecular weight of 150,000 or more in consideration of ductility and the like.
  • PVC can be represented by the molecular formula 2 below.
  • the plasticizer performs a function of curing the light-transmitting polymer resin and P(VC-VA) and converting them into a gel phase. Through this, the plasticizer may lower leakage current.
  • the plasticizer is not particularly limited, but may be DBA (Dibutyl Adipate).
  • the DBA may be represented by molecular formula 3 below.
  • the light-transmitting polymer resin and P(VC-VA) may have a weight ratio of 1:0.9 to 1:1.1.
  • the content of the light-transmitting polymer resin and P (VC-VA) is preferably 1:0.9 to 1:1.1, , more preferably 1:1.
  • the amount of the plasticizer added in the step of preparing the mixed solution may be 1:1 to 1:11, more preferably 1:1, based on the total weight of the light-transmitting polymer resin and P(VC-VA). to 1:3. If the plasticizer content is too low, the effect of adding the plasticizer may not appear, and if the plasticizer content is too high, deformation does not occur easily, so a lot of power is consumed for deformation or there is a risk of damage.
  • the variable focus lens 100 includes the composition for a variable focus lens described above.
  • the variable focus lens 100 includes a lens unit 110 made of a composition for a variable focus lens, an upper substrate 120 disposed above and below the lens unit 110, and a lower portion.
  • a substrate 130 may be included.
  • the upper substrate 120 and the lower substrate 130 may include a hollow in which the curved surface of the lens unit 110 is disposed, and may include an electrode contacting the lens unit 110 to allow current to flow.
  • FIG. 2 is a cross-section of the variable focus lens of FIG. 1, illustrating deformation of a lens unit according to supply of power.
  • FIG. 2(a) shows a case where current is not applied, FIG.
  • variable focus lens can control the shape of both sides according to the current application method.
  • a method for manufacturing a variable focus lens according to an embodiment of the present invention includes preparing a mixed solution by dissolving a mixture of a light-transmitting polymer resin, P(VC-VA), and a plasticizer in a solvent; and removing the solvent of the mixed solution.
  • the solvent may be a polar organic solvent. This is to easily dissolve the light-transmissive polymer resin and P(VC-VA).
  • the polar organic solvent may be any one of dioxane, tetrahydrofuran (THF), acetone, dimethyl sulfoxide (DMSO), dimethylformamide (DMF) and 1-methyl-2-pyrrolidone (NMP). .
  • the light-transmitting polymer resin, P(VC-VA), and the plasticizer have been previously described in the composition of the variable focus lens.
  • the weight ratio of the light-transmissive polymer resin and P(VC-VA) introduced in the step of preparing the mixed solution may be 1:0.9 to 1:1.1.
  • the content of the plasticizer added in the step of preparing the mixed solution may be 1:1 to 1:11 with respect to the total weight of the light-transmitting polymer resin and P(VC-VA).
  • Preparing the mixed solution includes preparing a solvent, preparing a light-transmitting polymer resin and P(VC-VA), mixing and dissolving the light-transmitting polymer resin and P(VC-VA) in the solvent, and a plasticizer It may include the step of mixing.
  • Preparing the light-transmitting polymer resin and P(VC-VA) may include purifying the light-transmitting polymer resin and P(VC-VA). Through this, the light-transmitting polymer resin and P(VC-VA) can be completely dissolved and dispersed in a solvent, and through this, the bonding structure between the light-transmitting polymer resin and P(VC-VA) can be improved to further increase ductility. there is.
  • the purifying step may include dissolving the light-transmitting polymer resin and P(VC-VA) in a polar solvent, precipitating the dissolved light-transmitting polymer resin and P(VC-VA) in an organic solvent, and drying the light-transmitting polymer. obtaining resin and P(VC-VA) powder.
  • Mixing the plasticizer may include stirring the mixed solution in a stirrer. This step may be performed under appropriate conditions so that the light-transmissive polymer resin, P(VC-VA) and the plasticizer are dissolved in a solvent, and may be performed at room temperature.
  • the step of removing the solvent from the mixed solution may include drying at room temperature and treating in a vacuum oven.
  • the drying at room temperature may be performed for 2 to 5 days, and then the solvent-reduced mixed solution may be put into a vacuum oven and treated at room temperature for 12 to 48 hours to remove the remaining solvent.
  • a step of injecting the mixed solution into a lens mold may be further included.
  • This step is a step of controlling the thickness and shape of the lens unit. This step may be performed during the step of removing the solvent of the mixed solution. After the solvent of the mixed solution is removed to some extent and the mixed solution has an appropriate viscosity, it may be put into a lens mold and the remaining solvent may be completely removed. Through this, the shape of the lens unit can be more easily controlled, and the surface state can be more excellently manufactured.
  • an upper substrate and a lower substrate may be disposed on the upper and lower portions of the lens unit, respectively.
  • the upper substrate and the lower substrate are the same as those described above.
  • THF (Sigma-Aldrich, 99.9%, CAS: 109-99-9) was prepared as a solvent, PVC powder (Scientific Polymer Products, Inc., Mw 275,000, CAS: 9002-86-2) and P (VC-VA ) powder (Scientific Polymer Products, Mw 115,000, CAS: 9003-22-9) was prepared.
  • PVC powder Scientific Polymer Products, Inc., Mw 275,000, CAS: 9002-86-2
  • P (VC-VA ) powder Scientific Polymer Products, Mw 115,000, CAS: 9003-22-9
  • the prepared PVC powder and 1 g of P(VC-VA) powder were mixed and completely dissolved in 10 ml of a THF solvent.
  • DBA Sigma-Aldrich, CAS: 105-99-7
  • 9 g was mixed with the above solution, and stirred for 4 hours at 400 rpm with a stirrer.
  • the mixed solution was poured into a glass dish and stored at room temperature for 3 days to remove the solvent.
  • the gelled mixed solution was put into a vacuum oven and treated for 24 hours to remove the solvent, thereby preparing a lens part of a variable focus lens.
  • a variable focus lens was manufactured by disposing an upper substrate and a lower substrate on the upper and lower portions of the lens unit, respectively.
  • XRD analysis was performed at 40 kV and 30 mA using an X-ray diffractometer (Empyrean, PANalytical). 3 shows the XRD analysis results. Referring to FIG. 3 , it can be seen that peaks indicating that the lens unit has an amorphous structure appear at 7 and 20 degrees. At this time, the higher the content of DBA, the thinner and clearer the peak. Through this analysis, it can be seen that the examples have microcrystals connected by amorphous polymer chains.
  • the relative permittivity was measured in the frequency range of 1 Hz to 1 MHz with a signal amplitude of 2 V at room temperature.
  • 5(a) is a graph measuring the relative permittivity of DBA and Comparative Example 1
  • FIG. 5(b) is a graph measuring the relative permittivity of Examples 1 to 5.
  • FIG. 5 in the case of Comparative Example 1, there was no change in the entire frequency range and a relatively low value was maintained.
  • the permittivity greatly increased in the low frequency range.
  • the higher the content of DBA the higher the dielectric constant in the low frequency range.
  • FIG. 6 is a graph measuring the impedance of DBA and Comparative Example 1
  • Figure 6 (b) is a graph measuring the impedance of Examples 1 to 5. Referring to FIG. 6 , it can be seen that impedance is reduced in a low frequency region due to the addition of DBA in Examples 1 to 5.
  • Examples 1 to 5 were prepared as dumbbell-shaped specimens and performed according to the ASTM D638 test method using a general-purpose tester (Tinius Olsen, H5KT). 7 shows the results of a stress-strain experiment. Referring to FIG. 7, Examples 1 and 2 showed a very high degree of deformation, Examples 3 and 4 showed a low degree of deformation, and Example 5 showed a tearing phenomenon even under low stress conditions.
  • variable focus lens 110: lens unit
  • 120 upper substrate
  • 130 lower substrate

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Engineering & Computer Science (AREA)
  • Manufacturing & Machinery (AREA)
  • Compositions Of Macromolecular Compounds (AREA)

Abstract

La présente invention concerne une composition pour une lentille à focale variable, une lentille à focale variable la comprenant, et son procédé de fabrication. Une composition pour lentille à focale variable selon un mode de réalisation de la présente invention comprend : une résine polymère transmettant la lumière ; du poly (chlorure de vinyle-co-acétate de vinyle) [P(VC-VA)] ; et un plastifiant.
PCT/KR2021/017077 2021-07-20 2021-11-19 Composition pour lentille à focale variable, lentille à focale variable la comprenant, et son procédé de fabrication WO2023003096A1 (fr)

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KR1020210094901A KR102532423B1 (ko) 2021-07-20 2021-07-20 가변 초점 렌즈용 조성물, 이를 포함하는 가변 초점 렌즈 및 그 제조방법
KR10-2021-0094901 2021-07-20

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Citations (5)

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Publication number Priority date Publication date Assignee Title
EP0137686A2 (fr) * 1983-09-08 1985-04-17 Minnesota Mining And Manufacturing Company Mélanges de polymères à haute absorption d'eau
KR100979253B1 (ko) * 2005-08-23 2010-08-31 세이코 프레시죤 가부시키가이샤 초점거리 가변 렌즈와 이를 이용한 초점거리 조절 장치 및촬상 장치
US20130242368A1 (en) * 2010-12-09 2013-09-19 Kilolambda Technologies Ltd. Fast response photochromic composition and device
KR20180114382A (ko) * 2017-04-10 2018-10-18 한국기술교육대학교 산학협력단 가변 초점 양볼록 렌즈
KR20200100657A (ko) * 2017-12-28 2020-08-26 닛토덴코 가부시키가이샤 광학 소자, 마이크로렌즈 어레이 및 광학 소자 제작방법

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US5757459A (en) * 1995-03-03 1998-05-26 Vision-Ease Lens, Inc. Multifocal optical elements
US6143558A (en) 1997-07-08 2000-11-07 The Regents Of The University Of Michigan Optical fiberless sensors for analyzing cellular analytes

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Publication number Priority date Publication date Assignee Title
EP0137686A2 (fr) * 1983-09-08 1985-04-17 Minnesota Mining And Manufacturing Company Mélanges de polymères à haute absorption d'eau
KR100979253B1 (ko) * 2005-08-23 2010-08-31 세이코 프레시죤 가부시키가이샤 초점거리 가변 렌즈와 이를 이용한 초점거리 조절 장치 및촬상 장치
US20130242368A1 (en) * 2010-12-09 2013-09-19 Kilolambda Technologies Ltd. Fast response photochromic composition and device
KR20180114382A (ko) * 2017-04-10 2018-10-18 한국기술교육대학교 산학협력단 가변 초점 양볼록 렌즈
KR20200100657A (ko) * 2017-12-28 2020-08-26 닛토덴코 가부시키가이샤 광학 소자, 마이크로렌즈 어레이 및 광학 소자 제작방법

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Title
BAE JIN WOO, CHOI DONG-SOO, YUN IN-HO, HAN DONG-HEON, OH SEUNG-JU, KIM TAE-HOON, CHO JEONG HO, LIN LIWEI, KIM SANG-YOUN: "Electrically Adaptive and Shape-Changeable Invertible Microlens", APPLIED MATERIALS & INTERFACES, AMERICAN CHEMICAL SOCIETY, US, vol. 13, no. 8, 3 March 2021 (2021-03-03), US , pages 10397 - 10408, XP093026718, ISSN: 1944-8244, DOI: 10.1021/acsami.0c21497 *

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