WO2010067741A1 - ハードコート剤及びこれを用いたプラスチックレンズ - Google Patents

ハードコート剤及びこれを用いたプラスチックレンズ Download PDF

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Publication number
WO2010067741A1
WO2010067741A1 PCT/JP2009/070303 JP2009070303W WO2010067741A1 WO 2010067741 A1 WO2010067741 A1 WO 2010067741A1 JP 2009070303 W JP2009070303 W JP 2009070303W WO 2010067741 A1 WO2010067741 A1 WO 2010067741A1
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WIPO (PCT)
Prior art keywords
hard coat
group
coat agent
same
carbon atoms
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Application number
PCT/JP2009/070303
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English (en)
French (fr)
Japanese (ja)
Inventor
渡辺　誠
伊藤　豊
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Hoya株式会社
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Publication of WO2010067741A1 publication Critical patent/WO2010067741A1/ja

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Classifications

    • 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
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/04—Polysiloxanes
    • C08G77/14—Polysiloxanes containing silicon bound to oxygen-containing groups
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D183/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Coating compositions based on derivatives of such polymers
    • C09D183/04—Polysiloxanes
    • C09D183/06—Polysiloxanes containing silicon bound to oxygen-containing groups
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
    • C09D7/40—Additives
    • C09D7/60—Additives non-macromolecular
    • C09D7/61—Additives non-macromolecular inorganic
    • C09D7/62—Additives non-macromolecular inorganic modified by treatment with other compounds
    • 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
    • G02B1/10—Optical coatings produced by application to, or surface treatment of, optical elements
    • G02B1/14—Protective coatings, e.g. hard coatings
    • 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
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/34—Silicon-containing compounds
    • C08K3/36—Silica
    • 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
    • C08K9/00—Use of pretreated ingredients
    • C08K9/02—Ingredients treated with inorganic substances
    • 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
    • C08K9/00—Use of pretreated ingredients
    • C08K9/04—Ingredients treated with organic substances
    • C08K9/06—Ingredients treated with organic substances with silicon-containing compounds

Definitions

  • the present invention relates to a hard coat agent constituting a cured film formed on a plastic substrate and a plastic lens using the same.
  • Molded products made of plastic materials are used in many fields because of their good dimensional stability, light weight, and workability.
  • such molded products also have a drawback of low hardness and inferior scratch resistance and weather resistance, and various developments have been made to improve this.
  • thermosetting hard coat agent is preferably used.
  • a metal oxide and a silane coupling agent has been proposed, and a silane-based cured film formed thereby has a skeleton that is basically close to glass, so that heat and ultraviolet rays are used.
  • a high refractive index film having a refractive index of 1.6 or more for example, composite oxide fine particles composed of titanium oxide, tin oxide, zirconium oxide or the like are used as the metal oxide, and the refractive index is 1.4 to 1.
  • silica particles in low refractive index coatings such as .6.
  • Patent Documents 1 to 3 propose a hard coat film using silica sol and a silane coupling agent.
  • the hard coating agents proposed in the above-mentioned Patent Documents 1 to 3 have a structure close to that of glass but are brittle and may easily crack. In addition, sufficient hardness has not been obtained yet in terms of scratch resistance. Also, the hard coating agent in the sol state (after hydrolysis) is highly unstable due to its high activity, and the formed film may become cloudy, which is problematic in practice. Moreover, due to this high activity, there has been a serious problem in productivity that the pot life of the hard coating agent itself is short.
  • the present invention when formed as a cured film on a plastic substrate, it is possible to improve the scratch resistance without the occurrence of fogging, and a hard coat agent with improved pot life,
  • An object of the present invention is to provide a plastic lens using the same.
  • the hard coat agent according to the present invention is a hard coat agent that is applied onto a plastic substrate to form a cured film, and is at least part of the particle surface replaced with aluminum? Or coated colloidal silica and the following general formula (1) R n —Si (OR ′) 4-n (1)
  • R is an organic group
  • R ′ is an alkyl group having 1 to 8 carbon atoms, an aryl group having 6 to 10 carbon atoms, an aralkyl group having 7 to 10 carbon atoms, or 2 to 10 is an acyl group
  • n is an integer of 1 to 4
  • the plurality of R may be the same or different
  • the plurality of OR ′ may be the same or different.
  • at least one acid among oxo acids is provided.
  • the hard coat agent of the present invention is adjusted to a pH of 4.5 or more and 6 or less by using oxo acid as a pH adjuster.
  • the plastic lens according to the present invention is configured such that a cured film is formed using the hard coat agent according to the present invention. That is, colloidal silica in which at least a part of the particle surface is replaced or coated with aluminum, and the following general formula (1) R n —Si (OR ′) 4-n (1)
  • R is an organic group
  • R ′ is an alkyl group having 1 to 8 carbon atoms, an aryl group having 6 to 10 carbon atoms, an aralkyl group having 7 to 10 carbon atoms, or 2 to 10 is an acyl group
  • n is an integer of 1 to 4
  • the plurality of R may be the same or different
  • the plurality of OR ′ may be the same or different.
  • a cured film made of a hard coat agent having an organosilicon compound and at least one acid among oxo acids is formed on a substrate made of plastic.
  • the colloidal silica contained in the hard coat agent as described above is colloidal silica in which at least a part of the particle surface is replaced or coated with aluminum.
  • the silica substitution or coating of silica sol is stable in the alkaline region, but can maintain a uniform dispersion state even in the acidic region. Therefore, the dispersed state of colloidal silica can be kept uniform even in the hard coating agent exhibiting acidity of the present invention, whereby the scratch resistance can be improved.
  • the pot life of the hard coat agent can be extended.
  • the present invention when formed as a cured film on a plastic substrate, it is possible to provide a hard coat agent that can improve scratch resistance without clouding and has an improved pot life. Further, by forming a cured film using this hard coat agent, it is possible to provide a plastic lens with suppressed fogging and improved scratch resistance.
  • the hard coating agent according to the present invention can be preferably applied to plastic lenses for eyeglasses, but can also be applied to other plastic lenses.
  • a primer layer for improving adhesion and impact resistance is formed on a lens substrate made of plastic as necessary, and the hard coat according to the present invention is formed thereon.
  • the agent is deposited and cured to form a cured film.
  • a plastic lens is formed by forming an antireflection film, a water-repellent film or the like as necessary.
  • the lens base material made of plastic is not particularly limited as long as it is a resin composition applicable to ordinary plastic lenses, and various materials can be used.
  • methyl methacrylate homopolymer, copolymer having methyl methacrylate and one or more other monomers as monomer components allyl diglycol carbonate (for example, diethylene glycol bisallyl carbonate homopolymer, and diethylene glycol bisallyl carbonate Copolymers containing one or more other monomers as monomer components), sulfur-containing copolymers, halogen-containing copolymers, polycarbonate, polystyrene, polyvinyl chloride, unsaturated polyester, polyethylene terephthalate, polyurethane, etc. alone Or a mixture of two or more can be used.
  • a material obtained by polymerizing diethylene glycol bisallyl carbonate for example.
  • the material when providing a primer layer between a base material and a cured film, the material will not be specifically limited if the adhesiveness and impact resistance of a base material and a cured film are improved and an optical characteristic is not affected.
  • the primer layer can be formed by applying a dipping method, a spin coating method, or a spray coating method, and then curing by heating or exposure.
  • an organosilicon compound colloidal silica in which at least a part of the particle surface is substituted or coated with Al (aluminum), and at least one of oxo acids 1 type of acid shall be contained.
  • the organosilicon compound at least one material represented by the following general formula (1) is used. R n —Si (OR ′) 4-n (1)
  • R is an organic group, for example, a monovalent having a functional group (amino group, isocyanate group, epoxy group, acrylic group, vinyl group, methacryl group, styryl group, ureido group, mercapto group).
  • a functional group amino group, isocyanate group, epoxy group, acrylic group, vinyl group, methacryl group, styryl group, ureido group, mercapto group.
  • Hydrocarbon groups having 3 to 20 carbon atoms such as ⁇ -aminopropyl group, N- ⁇ (aminoethyl) - ⁇ -aminopropyl group, N-phenyl- ⁇ -aminopropyl group, ⁇ -isocyanatopropyl group, ⁇ -Glycidoxypropyl group, ⁇ -epoxycyclohexylethyl group, ⁇ -acryloxypropyl group, vinyl group, ⁇ -methacryloxypropyl group, p-styryl group, ⁇ -ureidopropyl group, ⁇ -mercaptopropyl group, etc. It is done.
  • R ′ is an alkyl group having 1 to 8 carbon atoms, an aryl group having 6 to 10 carbon atoms, an aralkyl group having 7 to 10 carbon atoms, or an acyl group having 2 to 10 carbon atoms.
  • the alkyl group having 1 to 8 carbon atoms of R ′ may be linear, branched or cyclic, for example, methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl. Group, sec-butyl group, tert-butyl group, pentyl group, hexyl group, cyclopentyl group, cyclohexyl group and the like.
  • Examples of the aryl group include a phenyl group and a tolyl group.
  • Examples of the aralkyl group include a benzyl group and a phenethyl group.
  • Examples of the acyl group include an acetyl group.
  • N in the general formula (1) represents an integer of 1 to 4, and when there are a plurality of R, the plurality of R may be the same or different from each other, and the plurality of R ′ may be the same or different from each other. Good.
  • organosilicon compound represented by the general formula (1) examples include, for example, ⁇ -aminopropyltrimethoxysilane, ⁇ -aminopropyldimethoxymethylsilane, ⁇ -aminopropyltriethoxysilane, and ⁇ -aminopropyl.
  • methanol, ethanol, isopropanol propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol monobutyl ether, propylene glycol propyl ether, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol
  • the proportion of Al in the colloidal silica a material having a mass of 0.01% by mass to 5% by mass of the colloidal silica can be used. A part of the colloidal silica is replaced with Al (particularly, the surface of the particle is replaced with Al) or coated, thereby improving scratch resistance and wear resistance.
  • Al is less than 0.01% by mass of colloidal silica, the effect may not be sufficiently obtained. Further, if the amount is 5% by mass or less, the effect of scratch resistance is sufficiently obtained. Therefore, the content of Al atoms is preferably 0.01% by mass or more and 5% by mass or less of the colloidal silica.
  • an average particle diameter of colloidal silica a particle having a diameter of 5 nm to 30 nm can be suitably used.
  • the average particle size is less than 5 nm, there is a fear that sufficient scratch resistance cannot be obtained.
  • an average particle diameter exceeding 30 nm is used, there is a risk of affecting optical characteristics. For this reason, it is preferable to use a material having an average particle diameter of colloidal silica of 5 nm or more and 30 nm or less.
  • the hard coat agent contains at least one acid among oxo acids, and this acid is used for pH adjustment.
  • an oxo acid for pH adjustment for example, nitric acid, sulfuric acid, acetic acid, and other water-soluble organic carboxylic acids can be used.
  • the pH value when mixing the acid is preferably 4.5 or more and 6 or less when measured immediately after mixing.
  • Hard coating agents include a curing catalyst in an amount that can provide sufficient film hardness to promote the reaction, and various types for the purpose of improving wettability during application to a lens substrate and improving smoothness.
  • Organic solvents and surfactants (leveling agents) can also be included.
  • ultraviolet absorbers, antioxidants, light stabilizers and the like can be added as long as they do not affect the physical properties of the hard coat film.
  • the curing catalyst is not particularly limited, and examples thereof include amines such as allylamine and ethylamine, metal alkoxides, and metal chelate compounds thereof.
  • the hard coating agent thus prepared is formed on the lens substrate by, for example, dipping, spin coating, spraying, etc., and then cured by heating, light irradiation, etc., and a cured film is formed on the lens substrate. It is formed.
  • a hard coat agent according to the present invention and a plastic lens using the same were prepared and evaluated.
  • the evaluation items are as follows.
  • the same test was performed also on the plastic lens base material (referred to as a standard plastic lens) in which a cured film was not formed, and the Bayer value was obtained from the ratio of the amount of change in the haze value before and after both tests.
  • Hardness measurement was performed by a nanoindentation measurement method. The method is shown below. A glass plate was coated with a hard coating agent prepared under the conditions of Examples and Comparative Examples described later by dipping treatment, and thermoset at 110 ° C. for 1 hour to prepare a sample. An indentation test was performed on the surface of this sample with an ultra-fine indentation hardness tester (manufactured by Elionix, product name ENT-2100). For measurement of indentation, a regular triangular pyramid diamond indenter (vertical angle 65.03 °) with a ridge interval of 115 degrees was used and a load was applied at a load speed of 0.2 mgf / sec, and a maximum load of 0.98 mN was maintained for 1 second. Thereafter, unloading was performed at the same load speed.
  • Hard coat agent samples prepared according to Examples and Comparative Examples are stirred at a room temperature of 24 ° C. Periodically, the hard coating agent sample was taken out, coated on a glass plate by dipping, and a cured film was formed by thermal curing at 110 ° C. for 1 hour. The hardness of the cured film was measured by the above-mentioned nanoindentation method, and the decrease in hardness was examined. The evaluation criteria are shown below. ⁇ : Almost no change for 30 days or more, and there is no problem in using the hard coat agent. (Triangle
  • Example 1 a hard coating agent was prepared as follows. 30% by weight of methanol as a solvent was added to 17% by weight of an organosilicon compound ⁇ -GPS ( ⁇ -glycidoxypropyltrimethoxysilane, manufactured by Shin-Etsu Chemical Co., Ltd., product name KBM403). After stirring this for 10 minutes, 1.2% by weight of 1 mol / L nitric acid was added as a pH adjuster. Next, the solution was sufficiently stirred until the pH became constant under refrigeration at 5 ° C. to 10 ° C., and then colloidal silica in which at least a part of the particle surface was substituted with Al atoms was added.
  • ⁇ -GPS ⁇ -glycidoxypropyltrimethoxysilane, manufactured by Shin-Etsu Chemical Co., Ltd., product name KBM403
  • colloidal silica an average particle diameter of 5 to 30 nm and a material in which substituted Al atoms are 0.01 to 5% by weight of 1 particle of colloidal silica (product name Ludox AM, manufactured by GRACE) was used. . The addition amount was 44% by weight, and the mixture was stirred for 2 days under refrigeration at 5 to 10 ° C. At this time, the pH value was measured.
  • a hard coat agent sample was prepared by stirring for 4 days in this example.
  • the hard coat agent sample prepared as described above was applied by a dipping method on a glass plate and a substrate composed of diethylene glycol bisallyl carbonate (manufactured by HOYA, trade name HILUX, refractive index 1.50).
  • a cured film was formed on a glass plate or substrate by thermosetting at 110 ° C. for 1 hour after coating. And using this sample, said abrasion resistance, hardness, and the cloudiness of the film
  • Example 2 In this example, acetic acid was used instead of 1 mol / L nitric acid used as a pH adjuster in Example 1. Other than that was carried out similarly to Example 1, and formed the hard-coat agent and the cured film.
  • Example 3 In this example, a hard coat agent and a cured film were formed in the same manner as in Example 1 except that the addition amount of 1 mol / L nitric acid used as a pH adjuster in Example 1 was 1.4% by weight.
  • Example 4 In this example, a hard coat agent and a cured film were formed in the same manner as in Example 1 except that the addition amount of 1 mol / L nitric acid used as a pH adjuster in Example 1 was 0.4% by weight.
  • a hard coat agent and a cured film were formed as follows.
  • Comparative Example 1 In this example, in place of the Al-substituted colloidal silica used in Example 1, colloidal silica in which the particle surface is not substituted with Al atoms (manufactured by JGC Catalysts & Chemicals Co., Ltd., trade name Cataloid SI-40) is used. In the same manner as in Example 1, a hard coating agent and a cured film were formed.
  • Comparative Example 3 In this example, a hard coat agent and a cured film were formed in the same manner as in Example 1 except that 1 mol / L nitric acid used as a pH adjuster in Example 1 was omitted.
  • Comparative example 4 In this example, a hard coat agent and a cured film were formed in the same manner as in Example 1 except that the addition amount of 1 mol / L nitric acid used as a pH adjuster was five times that in Example 1.
  • Comparative Example 5 In this example, a hard coat agent and a cured film were formed in the same manner as in Example 1 except that the addition amount of 1 mol / L nitric acid used as a pH adjuster in Example 1 was 2.0% by weight.
  • Comparative Example 6 In this example, a hard coat agent and a cured film were formed in the same manner as in Example 1 except that the addition amount of 1 mol / L nitric acid used as a pH adjuster in Example 1 was 0.3% by weight.
  • Table 1 below shows the evaluation results in each example and comparative example.
  • the fine particles form hard nuclei upon curing, so that the hardness can be increased.
  • the dispersion state of the fine particles in the hard coat agent also greatly affects the hardness of the cured film formed from the hard coat agent and is required to be uniform.
  • colloidal silica in which at least a part of the particle surface is substituted with Al is used, the surface is charged in the hard coat agent, and a uniform dispersion state is obtained by repelling each other. Can do. It is obvious that the same effect can be obtained when colloidal silica coated with Al is used.
  • Comparative Example 3 in which no acid was added to the hard coat agent, the pH value was 7, and the pot life was less than 15 days. Furthermore, in Comparative Example 4 in which nitric acid is added in an amount five times that of Example 1, the pH value is as low as 3, and the results of Bayer value and nanoindentation hardness are both low. Furthermore, the pot life is less than 15 days.
  • Comparative Example 5 in which the pH value of the hard coating agent is 4, the Bayer value is 3.2, the nanoindentation hardness is 90, and the hardness is slightly decreased as compared with Example 3 in which the pH value is 4.5. Is seen. Further, in Comparative Example 6 having a pH value of 6.5, it was confirmed that the film was clouded. When the pH value exceeds 6, it can be predicted that clouding will start to occur.
  • the hard coat agent in the present invention exhibits acidity.
  • colloidal silica whose surface is replaced with aluminum or coated is stable even in the acidic region and can maintain a uniform dispersed state. For this reason, it is possible to improve the hardness as a hard coat film while extending the pot life.
  • pot life can be extended by adding colloidal silica partially coated with aluminum or coated with hard coating agent and oxo acid, and adjusting the pH. Further, by forming a hard coat film on a plastic lens using this hard coat agent, the hardness of the plastic lens can be increased and the wear resistance can be improved.
  • this invention is not limited to the structure demonstrated in the above-mentioned embodiment (and an Example), A various deformation

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Engineering & Computer Science (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Wood Science & Technology (AREA)
  • Materials Engineering (AREA)
  • Health & Medical Sciences (AREA)
  • Polymers & Plastics (AREA)
  • General Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Medicinal Chemistry (AREA)
  • Inorganic Chemistry (AREA)
  • Surface Treatment Of Optical Elements (AREA)
  • Paints Or Removers (AREA)
  • Eyeglasses (AREA)
PCT/JP2009/070303 2008-12-09 2009-12-03 ハードコート剤及びこれを用いたプラスチックレンズ WO2010067741A1 (ja)

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2014071394A (ja) * 2012-10-01 2014-04-21 Hoya Corp 眼鏡レンズの製造方法

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5968377A (ja) * 1982-10-14 1984-04-18 Toshiba Silicone Co Ltd 被覆用組成物及びその製造方法
JPH05306339A (ja) * 1991-03-11 1993-11-19 T S B:Kk 水性無機系組成物

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6680125B1 (en) * 1998-05-01 2004-01-20 Hoya Corporation Coating composition and method for preparing the same, and scuff-resistant plastic lense
JP2008065110A (ja) * 2006-09-08 2008-03-21 Seiko Epson Corp 防汚性光学物品
JP2008214397A (ja) * 2007-02-28 2008-09-18 Nikon-Essilor Co Ltd コーティング組成物及びそれを用いたプラスチックレンズ

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5968377A (ja) * 1982-10-14 1984-04-18 Toshiba Silicone Co Ltd 被覆用組成物及びその製造方法
JPH05306339A (ja) * 1991-03-11 1993-11-19 T S B:Kk 水性無機系組成物

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2014071394A (ja) * 2012-10-01 2014-04-21 Hoya Corp 眼鏡レンズの製造方法

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