JP2009227861A - Primer composition and plastic lens - Google Patents

Primer composition and plastic lens Download PDF

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Publication number
JP2009227861A
JP2009227861A JP2008076515A JP2008076515A JP2009227861A JP 2009227861 A JP2009227861 A JP 2009227861A JP 2008076515 A JP2008076515 A JP 2008076515A JP 2008076515 A JP2008076515 A JP 2008076515A JP 2009227861 A JP2009227861 A JP 2009227861A
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Prior art keywords
plastic lens
primer composition
primer
polyester resin
layer
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JP2008076515A
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Japanese (ja)
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Kotaro Ono
光太郎 小野
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Washi Kosan Co Ltd
ワシ興産株式会社
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Priority to JP2008076515A priority Critical patent/JP2009227861A/en
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Abstract

<P>PROBLEM TO BE SOLVED: To provide an aqueous dispersion type primer composition for obtaining a plastic lens of excellent hot-water resistance and impact resistance. <P>SOLUTION: This primer composition for forming a primer layer between a plastic lens base material and a hardcoating layer is an aqueous dispersion containing an acrylic-modified polyester resin, a crosslinking agent, and an acrylic rubber. The primer composition, comprising mainly a polyester resin of forming crosslinking structure by heat treatment, is crosslinked by the heat treatment to enhance durability against hot water and is added with the acrylic rubber to secure the impact resistance. <P>COPYRIGHT: (C)2010,JPO&INPIT

Description

  The present invention relates to a primer composition for forming a primer layer on a plastic lens substrate and a plastic lens having the primer layer.

  In recent years, plastic lenses that are lighter and more resistant to impact than inorganic glass are increasingly used. Since plastic lenses generally have the disadvantage of being easily damaged, a silicone-based hard coat layer is usually provided on the lens surface as a scratch-resistant coating. In addition, with the increase in the refractive index of plastic lenses, the use of a further antireflection film to suppress surface reflection has become mainstream.

  A plastic lens provided with both a hard coat layer and an antireflection film is improved in scratch resistance and light transmittance but has low impact resistance. Therefore, a primer layer is provided between the plastic lens substrate and the hard coat layer to serve as an impact buffer layer. The primer layer also contributes to improving the adhesion between the hard coat layer and the plastic lens substrate. As the primer layer, an organic solvent-based thermosetting polyurethane as disclosed in Japanese Patent No. 3130430 is suitably used, but a water-dispersed primer is being developed and penetrating from the environmental aspect.

As a water-dispersed primer composition, Japanese Patent No. 3362306 discloses a primer composition mainly composed of an ester-based thermoplastic elastomer. Thereby, it is said that it is excellent in heat resistance rather than what used the primer of the urethane type thermoplastic elastomer. However, the primer layer formed by the water-dispersed primer is not inherently excellent in water resistance, and is particularly weak against hot water. For this reason, when the plastic lens is dyed, the film is peeled off in a dye bath.
Japanese Patent No. 3301430 Japanese Patent No. 3362306

  The problem to be solved by the present invention is to provide a water-dispersed primer composition for obtaining a plastic lens excellent in hot water resistance and impact resistance.

  As a result of intensive studies to solve the above problems, the present inventors have improved the resistance to hot water by crosslinking a primer composition mainly composed of a polyester resin that forms a crosslinked structure by a heat treatment, Furthermore, the inventors have invented a water-dispersed primer composition that also has impact resistance by including acrylic rubber. That is, the primer composition of the present invention is a primer composition for forming a primer layer between a plastic lens substrate and a hard coat layer, and comprises an acrylic modified polyester resin, a crosslinking agent, and an acrylic rubber. It is characterized by being an aqueous dispersion containing.

  The acrylic modified polyester resin is preferably obtained by polymerizing a carboxylate-containing polyester resin and a glycidyl group-containing radical polymerizable vinyl monomer. By this method, an aqueous dispersion of an acrylic-modified polyester resin having a high graft ratio can be obtained. The reason is presumably due to the reaction between the carboxyl group of the carboxylate-containing polyester resin and the glycidyl group of the glycidyl group-containing radical polymerizable vinyl monomer.

  The carboxylate-containing polyester resin preferably has a molecular weight of 2,000 to 30,000. When the molecular weight is less than 2,000, the water resistance deteriorates, and when it exceeds 30,000, it becomes difficult to disperse in water.

  Examples of the glycidyl group-containing radical polymerizable vinyl monomer include glycidyl acrylate and glycidyl methacrylate.

  The crosslinking agent is preferably an epoxy group-containing crosslinking agent. The epoxy group of the epoxy group-containing crosslinking agent is presumed to react with the carboxyl group in the acrylic-modified polyester resin molecule to form a crosslinked structure, and therefore has one or more epoxy groups in one molecule of the epoxy group-containing crosslinking agent Is preferred. Examples of the epoxy group-containing crosslinking agent include glycerol diglycidyl ether, glycerol triglycidyl ether, neopentyl glycol diglycidyl ether, 1,6-hexanediol diglycidyl ether, ethylene propylene glycol diglycidyl ether, sorbitol polyglycidyl ether, sorbitan polyglycidyl Examples include ether, diglycerol polyglycidyl ether, adipic acid diglycidyl ester, and the like.

  In the blending of the epoxy group-containing crosslinking agent, the equivalent of the epoxy group of the epoxy group-containing crosslinking agent with respect to the carboxyl group of the acrylic-modified polyester resin is preferably between 0.2 and 5, and between 0.5 and 2 More preferably. When it is less than 0.2, sufficient hot water resistance cannot be obtained, and when it exceeds 5, adhesion to a plastic lens substrate is lowered.

  The primer composition of the present invention contains an elastic component for the purpose of improving the impact resistance of the primer layer. As the elastic component, acrylic rubber is selected from the viewpoint of water resistance and transparency. As the acrylic rubber, an acrylic rubber emulsion having a glass transition temperature of room temperature or less and a particle size of 2 μm or less is preferably used.

  The primer composition desirably contains fine particles of metal oxide and / or silica as a refractive index adjusting agent in order to suppress interference fringes. Examples of the metal element of the metal oxide include Al, Ti, Zr, Sn, Sb, W, In, Ce, Zn, Fe, La, and Ta. Among these metal oxides and silica, one kind or two or more kinds of fine particles are used. In recent years, composite fine particles comprising two or more kinds of oxides are preferably used, and a primer layer having a high refractive index and excellent weather resistance can be formed.

  The primer composition may contain other modifiers such as a UV absorber and a surfactant for improving smoothness.

  The plastic lens substrate is not particularly limited, and examples thereof include polymethyl methacrylate, polyallyl carbonate, polysulfone, polythiourethane, polythioepoxy, and copolymers thereof.

  The method for applying the primer composition is selected from known methods such as dipping and spin coating. The coating is cured at 80 to 120 ° C. for 2 to 60 minutes. It is preferable that the dry state of the coating film in the pre-curing is a dry-to-touch state because adhesion with a hard coat layer to be coated later is improved. After pre-curing the primer layer, the hard coat composition is applied, and the primer layer is fully cured simultaneously with the curing of the hard coat layer.

  The thickness of the primer layer is preferably 0.1 to 10 μm. If it is less than 0.1 μm, the impact resistance effect is reduced, and if it exceeds 10 μm, it is difficult to maintain surface accuracy.

  The hard coat layer as the scratch-resistant coating is preferably a silicone type. A catalyst, metal oxide particles, a diluent and the like can be mixed with the hydrolyzed organoalkoxysilane, and a surfactant, an ultraviolet absorber and the like can be added as necessary.

  Examples of the organoalkoxysilane hydrolyzate include α-glycidoxyethyltrimethoxysilane, β-glycidoxyethyltrimethoxysilane, γ-glycidoxypropyltrimethoxysilane, and γ-glycidoxypropylmethyldiethoxysilane. , Γ-methacryloxypropyltrimethoxysilane, glycidoxymethyltrimethoxysilane, trimethylchlorosilane, tetramethoxysilane, vinyltrimethoxysilane, methyltrimethoxysilane, tetramethoxysilane, etc., one of these Or 2 or more types can be used.

  Examples of the catalyst include organic carboxylic acids such as itaconic acid, metal alkoxides such as titanium alkoxide, metal complexes of acetylacetone aluminum and acetylacetone iron, alkali metal organic carboxylates such as sodium acetate and potassium acetate, and nitrogen-containing organics such as methylimidazole. There are compounds.

  It is desirable that the metal oxide fine particles contain fine particles of a refractive index adjusting agent metal oxide and / or silica in order to suppress interference fringes as in the primer composition. Examples of the metal element of the metal oxide include Al, Ti, Zr, Sn, Sb, W, In, Ce, Zn, Fe, La, and Ta. Among these metal oxides and silica, one kind or two or more kinds of fine particles are used. In recent years, composite fine particles composed of two or more kinds of oxides are preferably used, and a hard coat layer having a high refractive index and excellent weather resistance can be formed.

  As the diluent, polar solvents such as alcohols, ethers, esters and cellosolves are effective.

An antireflection film is usually provided on the hard coat layer. The anti-reflective film fixes SiO 2 , ZrO 2 , TiO 2 , Al 2 O 3 etc. by vacuum deposition, sputtering, ion plating method, etc., and also fixes fluorine-based amorphous organic substances by dipping method. There is an organic antireflection film.

  With the primer composition of the present invention, a primer layer excellent in hot water resistance can be formed, and the plastic lens formed with the primer layer is excellent in dyeability and impact resistance.

  Embodiments of the present invention will be described below.

[Example 1]
(1) Preparation of primer composition 40 parts by weight of an aqueous dispersion “Pesresin A-215GE” (manufactured by Takamatsu Yushi Co., Ltd.) containing an acrylic-modified polyester resin and an epoxy group-containing crosslinking agent, a carboxyl-modified acrylic rubber emulsion 10 parts by weight of “SX-8900E” (manufactured by JSR Corporation), 40 parts by weight of colloidal silica sol “Sun Colloid O-40” (manufactured by Nissan Chemical Industries, Ltd., solid content concentration: 40%), 5 weight of ion-exchanged water as a solvent A primer composition containing 5 parts by weight of methoxypropanol and 5 parts by weight of methoxypropanol was prepared.
(2) Formation of primer layer on plastic lens base material This primer composition was converted into a plastic lens base material A made of diethylene glycol bisallyl carbonate resin (a lens base obtained by polymerizing and curing a monomer “RAV-7” manufactured by Great Lakes Chemical Italy). Material, refractive index: 1.48) and plastic lens base material B made of polythiourethane resin (a lens base material obtained by polymerizing and curing a monomer “MR-8” manufactured by Mitsui Chemicals, Inc., refractive index: 1.60) The primer layer was applied by a dipping method (pickup speed: 10 to 150 mm / min), preliminarily cured by heat treatment at 90 ° C. for 2 minutes, and a primer layer in a dry touch state was formed.
(3) Application and curing of silicone-based hard coat composition A silicone hard coat composition “Crystal Coat C-337” (manufactured by SDC Technologies Asia Co., Ltd.) of the plastic lens obtained in (2) is used. It was applied on the primer layer by a dipping method (pickup speed 10 to 100 mm / min), and the plastic lens was thermally cured at 100 to 120 ° C. for 3 hours.
(4) Formation of antireflection film A five-layer antireflection film composed of SiO 2 and ZrO 2 was formed on the hard coat of the plastic lens obtained in (3) by a vacuum deposition method.

[Example 2]
(1) Preparation of primer composition 40 parts by weight of an aqueous dispersion “Pesresin A-215GE” (manufactured by Takamatsu Yushi Co., Ltd.) containing an acrylic-modified polyester resin and an epoxy group-containing crosslinking agent, a carboxyl-modified acrylic rubber emulsion “SX-8900J” (manufactured by JSR Corporation) 10 parts by weight, titanium dioxide-based metal oxide sol “Sun Colloid HT-327M6” (manufactured by Nissan Chemical Industries, Ltd., solid content concentration: 30%) 40 parts by weight, as solvent A primer composition containing 5 parts by weight of ion-exchanged water and 5 parts by weight of methanol was prepared.
(2) Formation of primer layer on plastic lens base material This primer composition is made from a plastic lens base material C made of polythiourethane resin (a lens base material obtained by polymerizing and curing a monomer “MR-7” manufactured by Mitsui Chemicals, Inc.) 1.67) and a plastic lens substrate D made of polythioepoxy resin (a lens substrate obtained by polymerizing and curing a monomer “MR-174” manufactured by Mitsui Chemicals, Inc., refractive index: 1.74) At a speed of 10 to 150 mm / min), and heat-treated at 90 ° C. for 2 minutes to be pre-cured to form a primer layer in a dry-to-touch state.
(3) Application and curing of silicone hard coat composition A silicone hard coat composition “Crystal Coat C-410” (manufactured by SDC Technologies Asia Co., Ltd.) of the plastic lens obtained in (2) is used. It was applied on the primer layer by a dipping method (pulling speed of 10 to 150 mm / min), and the plastic lens was thermally cured at 100 to 120 ° C. for 3 hours.
The antireflection film was formed in the same manner as in Example 1 to obtain a plastic lens.

[Example 3]
(1) Preparation of primer composition 40 parts by weight of an aqueous dispersion “Pesresin A-215GE” (manufactured by Takamatsu Yushi Co., Ltd.) containing an acrylic-modified polyester resin and an epoxy group-containing crosslinking agent, a carboxyl-modified acrylic rubber emulsion 10 parts by weight of “SX-8900F” (manufactured by JSR Corporation), 40 parts by weight of tin dioxide based metal oxide sol “Sun Colloid HX-305M5” (manufactured by Nissan Chemical Industries, Ltd., solid content concentration: 30%), as solvent A primer composition containing 5 parts by weight of ion-exchanged water and 5 parts by weight of methanol was prepared.
A plastic lens was obtained in the same manner as in Example 2 except that this primer composition was used.

[Example 4]
(1) Preparation of primer composition 40 parts by weight of an aqueous dispersion “Pesresin A-215GE” (manufactured by Takamatsu Yushi Co., Ltd.) containing an acrylic-modified polyester resin and an epoxy group-containing crosslinking agent, a carboxyl-modified acrylic rubber emulsion A primer composition containing 10 parts by weight of “SX-8900F” (manufactured by JSR Corporation) and 5 parts by weight of ion-exchanged water and 5 parts by weight of methanol as a solvent was prepared.
A plastic lens was obtained in the same manner as in Example 2 except that this primer composition was used.

[Comparative Example 1]
(1) Preparation of primer composition Water dispersion of thermoplastic polyester elastomer “Pesresin A-160P” (manufactured by Takamatsu Yushi Co., Ltd.) 40 parts by weight, carboxyl-modified acrylic rubber emulsion “SX-8900E” (manufactured by JSR Corporation) ) 10 parts by weight, titanium dioxide-based metal oxide sol "Sun Colloid HT-327M6" (Nissan Chemical Industry Co., Ltd., solid content concentration: 30%) 40 parts by weight, 5 parts by weight of ion-exchanged water and 5 parts by weight of methanol as a solvent A primer composition having a part as a mixed solution was prepared.
A plastic lens was obtained in the same manner as in Example 2 except that this primer composition was used.

[Comparative Example 2]
(1) Preparation of primer composition Water dispersion of thermoplastic polyester elastomer “Pesresin A-160P” (manufactured by Takamatsu Yushi Co., Ltd.) 40 parts by weight, carboxyl-modified acrylic rubber emulsion “SX-8900E” (manufactured by JSR Corporation) ) 10 parts by weight, tin dioxide based metal oxide sol “Sun Colloid HX-305M5” (manufactured by Nissan Chemical Industries, Ltd., solid content concentration: 31%) 40 parts by weight, 5 parts by weight of ion-exchanged water and 5 parts by weight of methanol as a solvent A primer composition having a part as a mixed solution was prepared.
A plastic lens was obtained in the same manner as in Example 2 except that this primer composition was used.

[Evaluation]
Each evaluation of the obtained plastic lens was implemented as follows. The results are shown in Table 1.
1) Appearance The transmitted light and reflected light were applied to a plastic lens under a three-wavelength daylight white fluorescent lamp, and the degree of interference fringes and the whitening state were visually observed and judged.
2) Initial adhesion A cross-cut test conforming to the JIS K 5600 standard was performed, and the adhesiveness of the coated film was observed and judged after peeling 10 times with an adhesive tape “Cello Tape (registered trademark) CT-24” (manufactured by Nichiban Co., Ltd.). did. In 100 枡 (denominator), the number of folds that do not peel is expressed in the numerator.
3) Scratch resistance
Steel wool # 0000 conforming to the JIS K 5600 standard was used, and the degree of damage to the coating film at 10 reciprocations / 15 seconds at a load of 500 g and 1 kg was determined.
○: 2/3 or more of the number of evaluated lenses is acceptable Δ: 1/3 or more of the number of evaluated lenses is less than 2/3 is acceptable ×: Less than 1/3 of the number of evaluated lenses is acceptable 4) Dyeing antireflection film For the plastic lens with hard coat before formation, the molecular dye Black color manufactured by BPI was used, and the dyeing density and coating film adhesion at 92 ° C. for 10 minutes and 96 ° C. for 45 minutes were observed and judged.
○: 2/3 or more of the number of evaluated lenses is acceptable Δ: 1/3 or more of the number of evaluated lenses is less than 2/3 is acceptable ×: Less than 1/3 of the number of evaluated lenses is acceptable 5) Warm water resistance and heat resistance It was immersed in aqueous hot water 60 ° C. for 10 minutes and 90 ° C. for 10 minutes, and the adhesion of the coating film and the presence or absence of appearance cracks were determined.
○: 2/3 or more of the number of evaluated lenses is acceptable Δ: 1/3 or more of the number of evaluated lenses is less than 2/3 is acceptable X: Less than 1/3 of the number of evaluated lenses is acceptable 6) Salt water boiling test reflection prevention The plastic lens with a hard coat before film formation was immersed in brine boiling water for 15 minutes and then cooled for 15 minutes, and the adhesion and appearance cracks of the coating film were observed and judged.
○: 2/3 or more of the number of evaluated lenses is acceptable Δ: 1/3 or more of the number of evaluated lenses is less than 2/3 is acceptable ×: Less than 1/3 of the number of evaluated lenses is acceptable 7) Impact resistance ANSI Z87 .1 A ball drop test according to the standard was performed, and the degree of “crack, chip, and crack” with respect to energy (0.816 joule) four times that of the FDA standard (0.204 joule) was observed and judged.
8) Weather-resistant adhesion Using a QUV tester, the adhesion and appearance cracks after exposing the lens A surface for 240 hours were observed and judged.
○: 2/3 or more of the number of evaluated lenses is acceptable Δ: 1/3 or more and less than 2/3 of the number of evaluated lenses is acceptable ×: Less than 1/3 of the number of evaluated lenses is acceptable

Claims (6)

  1.   A primer composition for forming a primer layer between a plastic lens substrate and a hard coat layer, wherein the primer is an aqueous dispersion containing an acrylic-modified polyester resin, a crosslinking agent, and acrylic rubber Composition.
  2.   The primer composition according to claim 1, wherein the acrylic-modified polyester resin is obtained by polymerizing a carboxylate-containing polyester resin and a glycidyl group-containing radical polymerizable vinyl monomer.
  3.   The primer composition according to claim 1 or 2, wherein the crosslinking agent is an epoxy group-containing crosslinking agent.
  4.   The primer composition according to any one of claims 1 to 3, comprising fine particles of metal oxide and / or silica.
  5.   A plastic lens, wherein a primer layer formed from the primer composition according to any one of claims 1 to 4 is interposed between the plastic lens substrate and the hard coat layer.
  6.   6. The plastic lens according to claim 5, wherein an antireflection film layer is formed on the hard coat layer.
JP2008076515A 2008-03-24 2008-03-24 Primer composition and plastic lens Pending JP2009227861A (en)

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Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2010134090A (en) * 2008-12-03 2010-06-17 Asahi Lite Optical Co Ltd Method of manufacturing plastic lens for glasses having organic anti-reflection film
JP2012226026A (en) * 2011-04-18 2012-11-15 Tokuyama Corp Photochromic lens
JP2014085528A (en) * 2012-10-24 2014-05-12 Teijin Dupont Films Japan Ltd White reflection film
WO2014178517A1 (en) * 2013-04-30 2014-11-06 주식회사 엘지화학 Polyester-based primer composition, optical film using same and polarizing plate comprising same
JP2016102218A (en) * 2009-09-25 2016-06-02 ベック株式会社 Coating material

Citations (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS63270123A (en) * 1987-04-30 1988-11-08 Dainippon Printing Co Ltd Plastic lens and its manufacture
JPH04182109A (en) * 1990-11-16 1992-06-29 Hoya Corp Manufacture of plastic lens
JPH04294302A (en) * 1991-03-22 1992-10-19 Olympus Optical Co Ltd Composite type optical part
JPH10166517A (en) * 1996-12-16 1998-06-23 Fuji Photo Film Co Ltd Easily bondable film
JP2000144048A (en) * 1998-11-13 2000-05-26 Ito Kogaku Kogyo Kk Primer composition
JP2000351987A (en) * 1999-05-10 2000-12-19 Takasago Internatl Corp Substituted phenols as pfrfume, flavor and antimicrobial compound
JP2001287308A (en) * 2000-02-04 2001-10-16 Toray Ind Inc Plastic laminate and image display protecting film
JP2002322225A (en) * 2001-02-26 2002-11-08 Toyo Ink Mfg Co Ltd Modified polyester resin and resin composition using the resin
JP2004341052A (en) * 2003-05-13 2004-12-02 Ito Kogaku Kogyo Kk Optical element
JP2008046282A (en) * 2006-08-12 2008-02-28 Washi Kosan Co Ltd Progressive multifocal plastic lens for high refractivity eyeglasses

Patent Citations (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS63270123A (en) * 1987-04-30 1988-11-08 Dainippon Printing Co Ltd Plastic lens and its manufacture
JPH04182109A (en) * 1990-11-16 1992-06-29 Hoya Corp Manufacture of plastic lens
JPH04294302A (en) * 1991-03-22 1992-10-19 Olympus Optical Co Ltd Composite type optical part
JPH10166517A (en) * 1996-12-16 1998-06-23 Fuji Photo Film Co Ltd Easily bondable film
JP2000144048A (en) * 1998-11-13 2000-05-26 Ito Kogaku Kogyo Kk Primer composition
JP2000351987A (en) * 1999-05-10 2000-12-19 Takasago Internatl Corp Substituted phenols as pfrfume, flavor and antimicrobial compound
JP2001287308A (en) * 2000-02-04 2001-10-16 Toray Ind Inc Plastic laminate and image display protecting film
JP2002322225A (en) * 2001-02-26 2002-11-08 Toyo Ink Mfg Co Ltd Modified polyester resin and resin composition using the resin
JP2004341052A (en) * 2003-05-13 2004-12-02 Ito Kogaku Kogyo Kk Optical element
JP2008046282A (en) * 2006-08-12 2008-02-28 Washi Kosan Co Ltd Progressive multifocal plastic lens for high refractivity eyeglasses

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2010134090A (en) * 2008-12-03 2010-06-17 Asahi Lite Optical Co Ltd Method of manufacturing plastic lens for glasses having organic anti-reflection film
JP2016102218A (en) * 2009-09-25 2016-06-02 ベック株式会社 Coating material
JP2012226026A (en) * 2011-04-18 2012-11-15 Tokuyama Corp Photochromic lens
JP2014085528A (en) * 2012-10-24 2014-05-12 Teijin Dupont Films Japan Ltd White reflection film
WO2014178517A1 (en) * 2013-04-30 2014-11-06 주식회사 엘지화학 Polyester-based primer composition, optical film using same and polarizing plate comprising same
US9110244B2 (en) 2013-04-30 2015-08-18 Lg Chem, Ltd. Polyester-based primer composition, optical film and polarizing plate comprising

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