WO2017204327A1 - Plaque de polarisation ignifuge, et dispositif d'affichage à cristaux liquides mettant en œuvre celle-ci - Google Patents

Plaque de polarisation ignifuge, et dispositif d'affichage à cristaux liquides mettant en œuvre celle-ci Download PDF

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Publication number
WO2017204327A1
WO2017204327A1 PCT/JP2017/019690 JP2017019690W WO2017204327A1 WO 2017204327 A1 WO2017204327 A1 WO 2017204327A1 JP 2017019690 W JP2017019690 W JP 2017019690W WO 2017204327 A1 WO2017204327 A1 WO 2017204327A1
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Prior art keywords
layer
meth
polarizing plate
mass
flame
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PCT/JP2017/019690
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English (en)
Japanese (ja)
Inventor
義孝 武市
彰雄 矢内
浩和 狩野
典明 望月
Original Assignee
日本化薬株式会社
株式会社ポラテクノ
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Application filed by 日本化薬株式会社, 株式会社ポラテクノ filed Critical 日本化薬株式会社
Priority to JP2018519629A priority Critical patent/JPWO2017204327A1/ja
Priority to CN201780025387.8A priority patent/CN109073816A/zh
Priority to KR1020187033178A priority patent/KR20190013751A/ko
Publication of WO2017204327A1 publication Critical patent/WO2017204327A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
    • C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
    • C08F20/10—Esters
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/30—Polarising elements
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
    • C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
    • C08F20/10—Esters
    • C08F20/12—Esters of monohydric alcohols or phenols
    • C08F20/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
    • C08F20/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F230/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal
    • C08F230/02—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing phosphorus
    • 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
    • C08K5/0066—Flame-proofing or flame-retarding additives
    • 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
    • C08K5/49—Phosphorus-containing compounds
    • C08K5/51—Phosphorus bound to oxygen
    • C08K5/53—Phosphorus bound to oxygen bound to oxygen and to carbon only
    • C08K5/5313—Phosphinic compounds, e.g. R2=P(:O)OR'
    • 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
    • C08K5/49—Phosphorus-containing compounds
    • C08K5/5399—Phosphorus bound to nitrogen
    • G—PHYSICS
    • G02—OPTICS
    • G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
    • G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
    • G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour 
    • G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour  based on liquid crystals, e.g. single liquid crystal display cells
    • G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
    • G02F1/1333—Constructional arrangements; Manufacturing methods
    • G02F1/1335—Structural association of cells with optical devices, e.g. polarisers or reflectors

Definitions

  • the present invention relates to a liquid crystal display device using the flame retardant polarizing plate.
  • Liquid crystal displays starting from small displays such as watches and calculators are also available for personal computers, LCD TVs, liquid crystal projectors, in-vehicle instrument panels, in-vehicle center console panels, in-vehicle navigation systems, and head-ups. -It has come to be used as an on-vehicle monitor for displays and the like.
  • in-vehicle modules were provided with a polycarbonate plate, an acrylic plate, a louver jig, etc. as a front plate of the display in order to protect the display.
  • a front plate of the display in order to protect the display.
  • such a front plate has been removed, and the display has come to appear on the interior surface of the vehicle. For this reason, the flame retardance required for the display is further increased.
  • the polarizing plate which is a constituent element of the liquid crystal display, burns, the display function of the liquid crystal monitor is lost and safety information is not displayed, which increases the risk. Therefore, “the performance that does not burn” and / or “the performance that disappears even when burned” is also strongly required for the polarizing plate bonded to the outermost surface of the display.
  • the cost of insurance may be lowered, and in recent years, home appliances are also demanding flame retardancy.
  • flame retardancy is required for home appliances and in-vehicle displays, and flame retardancy is also required for polarizing plates.
  • a polarizing plate is formed on both surfaces of a polarizing element obtained by adsorbing iodine or a dichroic dye as a dichroic dye on a polyvinyl alcohol (hereinafter also referred to as “PVA”) film and stretching it.
  • PVA polyvinyl alcohol
  • An acetyl cellulose (hereinafter also referred to as “TAC”) film is laminated and adhered, and a pressure-sensitive adhesive layer (hereinafter also referred to as “PSA”) is further provided on the TAC film surface.
  • TAC acetyl cellulose
  • PSA pressure-sensitive adhesive layer
  • PVA, TAC, and PSA are the same components as general plastic and cellulose film, so they do not have the “non-burning performance” and “performance that disappear even when burned” required for in-vehicle modules. Have sex. Therefore, a technique for making the polarizing plate flame-retardant has been demanded.
  • TAC contains triphenyl phosphate (hereinafter also referred to as “TPP”) as a plasticizer. It is described in Patent Document 1 that flame retardancy is imparted by containing such a phosphorus compound, and it is known to be applied to a polarizing plate.
  • TPP triphenyl phosphate
  • Patent Document 2 describes that a flame-retardant woven fabric is made into a geometric pattern.
  • Patent Document 3 describes a technique in which a pressure-sensitive adhesive contains at least 10% by mass of a halogen-free flame retardant such as a phosphate ester.
  • the number of films constituting the polarizing plate is increasing year by year.
  • a polarizing plate having a retardation plate having broadband achromatic property is known to have a quarter-wave plate and a half-wave plate, and an adhesive layer for laminating them is required.
  • the number of films for satisfying necessary functions such as hard coat layer (HC layer), antireflection layer or antiglare layer for preventing scratches and antireflection on the surface is required.
  • the increase in the number of laminated films is a cause of further increasing the flame retardancy of the polarizing plate. In a situation where flammability is increasing due to an increase in the number of layers, there is a demand for imparting flame retardancy.
  • an object of the present invention is to provide a flame retardant polarizing plate capable of realizing high flame retardancy, especially “performance not burning” and / or “performance disappearing even when burned” and a liquid crystal display device using the same. Is to provide.
  • the present invention has at least one of high transparency, high degree of polarization, high temperature or high temperature and high humidity durability (there is little deterioration even when exposed to high temperature or high temperature and high humidity for a long time).
  • the present inventors have determined that a predetermined amount of a halogen-free flame retardant having one or more (meth) acryloyl groups or a halogen-free flame retardant having no (meth) acryloyl groups.
  • a cured product of a resin composition containing a (meth) acrylate compound that does not contain halogen and does not exhibit flame retardancy, or a resin containing a predetermined amount of a halogen-free flame retardant having one or more (meth) acryloyl groups A polarizing plate characterized in that a layer having a specific thickness including a cured product of the composition is provided on the surface layer side with respect to the polarizing element is highly transparent, has a high degree of polarization, and has a high temperature and a high temperature. We have found that we can achieve a polarizing plate that achieves a high level of flame retardancy and high performance that does not burn even when exposed to high humidity for long periods of time. It came to do.
  • a polarizing plate comprising a layer containing 5 to 99% by mass of a compound having a phosphaphenanthrene skeleton and / or a compound having a phosphazene skeleton has high transparency and a high degree of polarization.
  • a polarizing plate that has little deterioration even when exposed to high temperatures, high temperatures and high humidity for a long period of time and has high flame resistance, in particular, ⁇ performance that does not burn '' and ⁇ performance that disappears even when burned ''
  • the headline and the present invention were completed.
  • the present invention relates to the following [X1] to [X10].
  • [X1] Halogen-free flame retardant having one or more (meth) acryloyl groups or halogen-free flame retardant not having (meth) acryloyl groups, 5 to 80% by mass, containing no halogen and showing no flame retardancy
  • a flame-retardant polarizing plate comprising a flame-retardant layer having a thickness of 1 to 100 ⁇ m and a polarizing element.
  • a halogen-free flame retardant having one or more (meth) acryloyl groups and a halogen-free flame retardant having no (meth) acryloyl groups are a 10-oxo-9-oxa-10-phosphaphenanthrene skeleton or phosphazene
  • the flame-retardant polarizing plate according to [X1] which is a compound having a skeleton.
  • [X3] The compound having a 10-oxo-9-oxa-10-phosphaphenanthrene skeleton is represented by the formula (1): (In the formula, R 1 is a (meth) acryloyl group or a substituent having a (meth) acryloyl group)
  • the flame-retardant polarizing plate as described in [X2] which is a compound represented by these.
  • [X4] The flame retardant polarizing plate according to [X2], wherein the compound having a phosphazene skeleton is a compound having a 1,3,5,2,4,6-triazatriphospholine skeleton.
  • the halogen-free flame retardant having one or more (meth) acryloyl groups has two or more (meth) acryloyl groups, Any of [X1] to [X5], wherein a mass ratio of the halogen-free flame retardant having two or more (meth) acryloyl groups to the (meth) acrylate compound in the resin composition is 10:88 to 75:23
  • [X8] The flame retardant polarizing plate according to any one of [X1] to [X7], wherein the flame retardant layer is a layer selected from the group consisting of an adhesive layer, an adhesive layer, a hard coat layer, and a protective layer.
  • the flame retardant layer is a layer selected from the group consisting of an adhesive layer, an adhesive layer, a hard coat layer, and a protective layer.
  • a liquid crystal display device comprising the flame-retardant polarizing plate according to any one of [X1] to [X9].
  • the present invention relates to the following [Y1] to [Y10].
  • [Y1] A flame-retardant polarizing plate containing a compound having a phosphaphenanthrene skeleton and / or a compound having a phosphazene skeleton in an amount of 5 to 99% by mass and having a thickness of 0.1 to 100 ⁇ m and a polarizing element .
  • the flame retardant layer is 5 to 80% by mass of a compound having a phosphaphenanthrene skeleton and / or a compound having a phosphazene skeleton, and is different from the compound having the phosphaphenanthrene skeleton and the compound having the phosphazene skeleton (meta 10) to 99.9 of a cured product of a resin composition containing an acrylate compound, a compound having a phosphaphenanthrene skeleton having a (meth) acryloyl group and / or a compound having a phosphazene skeleton having a (meth) acryloyl group.
  • [Y3] The flame-retardant polarizing plate according to [Y1] or [Y2], wherein the compound having a phosphaphenanthrene skeleton is a compound having a 10-oxo-9-oxa-10-phosphaphenanthrene skeleton.
  • [Y4] The compound having a 10-oxo-9-oxa-10-phosphaphenanthrene skeleton is represented by the formula (1): (In the formula, R 1 is a (meth) acryloyl group or a substituent having a (meth) acryloyl group)
  • the flame-retardant polarizing plate as described in [Y3] which is a compound represented by these.
  • [Y5] The flame-retardant polarizing plate according to [Y1] or [Y2], wherein the compound having a phosphazene skeleton is a compound having a 1,3,5,2,4,6-triazatriphosphorine skeleton.
  • the compound having the 1,3,5,2,4,6-triazatriphosphorine skeleton has the formula: (Wherein R 2 to R 7 are each independently a (meth) acryloyl group or a substituent having the same)
  • the flame-retardant polarizing plate as described in [Y5] which is a compound represented by these.
  • [Y7] The flame retardant polarizing plate according to any one of [Y2] to [Y6], wherein all or part of the (meth) acrylate compound has a hydroxyl group and is contained in the resin composition in an amount of 25 to 90% by mass.
  • [Y8] The flame retardant polarizing plate according to any one of [Y1] to [Y7], wherein the flame retardant layer is a layer selected from the group consisting of an adhesive layer, an adhesive layer, a hard coat layer, and a protective layer.
  • a liquid crystal display device comprising the flame retardant polarizing plate according to any one of [Y1] to [Y9].
  • the flame-retardant polarizing plate of the present invention and a liquid crystal display device using the same have high flame retardancy, and in particular, “performance that does not burn” (non-flammability) and / or “performance that flames disappear even when burned” ( Can be realized.
  • the present invention has at least one property of “high transparency”, “high degree of polarization”, and “high temperature or high temperature and high humidity durability”.
  • the flame retardant layer used in the present invention (hereinafter, also referred to as “FR layer” (Frame Resistance layer))
  • FR layer Framework layer
  • the flame retardant layer used in the present invention is a flame retardant layer (C) containing a compound having a phosphaphenanthrene skeleton and / or a compound having a phosphazene skeleton.
  • the flame-retardant polarizing plate according to the present invention is a flame-retardant polarizing plate including at least one selected from the flame-retardant layers (A), (B), and (C) and a polarizing element. To do.
  • flame retardant means that it does not burn above a certain speed (it is difficult to burn), or that an ignited flame digests or does not spread beyond a certain range. Indicates that the interior material flammability test FMVSS 302 is satisfied. “Flame retardant” is a compound for imparting flame retardancy.
  • the flame retardant layer (A) comprises (a) a predetermined amount of a halogen-free flame retardant having one or more (meth) acryloyl groups or a halogen-free flame retardant having no (meth) acryloyl groups, and (b) It is a flame retardant layer containing a cured product of a resin composition containing a (meth) acrylate compound that does not contain halogen and does not exhibit flame retardancy.
  • a halogen-free flame retardant is a halogen-free flame retardant having one or more (meth) acryloyl groups or a halogen-free flame retardant having no (meth) acryloyl groups.
  • the (meth) acryloyl group represents an acryloyl group or a methacryloyl group.
  • Halogen-free means that the compound does not contain halogen atoms such as fluorine, chlorine, bromine and iodine atoms.
  • the content of the halogen-free flame retardant in the resin composition is 5 to 80% by mass, preferably 15 to 75% by mass, more preferably 25 to 70% by mass, and particularly preferably 35 to 65% by mass.
  • the halogen-free flame retardant is preferably a compound having a phosphaphenanthrene skeleton or a phosphazene skeleton.
  • the flame retardant performance can be remarkably improved.
  • the phosphazene skeleton is a cyclotriphosphazene skeleton
  • the flame retardancy function can be particularly improved.
  • the compound having a phosphaphenanthrene skeleton, the compound having a phosphazene skeleton, and the compound having a cyclotriphosphazene skeleton may be used singly or in a combination of two or more.
  • the flame retardant having a phosphaphenanthrene skeleton is preferably a compound having a 10-oxo-9-oxa-10-phosphaphenanthrene skeleton.
  • a compound having a 10-oxo-9-oxa-10-phosphaphenanthrene skeleton has the formula (1): It is preferable that it is a compound represented by these.
  • R 1 is preferably hydrogen, an unsubstituted or substituted alkyl group having 1 to 4 carbon atoms, an alkoxyl group having 1 to 4 carbon atoms, an unsubstituted or substituted phenyl group Group, unsubstituted or substituted naphthyl group, unsubstituted or substituted phenoxy group, substituted amide group, aryl group having 1 to 4 carbon atoms or alkoxyl group having 1 to 4 carbon atoms , An alkyl ether group having a C 1-4 alkyl group having a substituent, a (meth) acryloyl group, and a substituent having a (meth) acryloyl group.
  • the substituent for the alkyl group having 1 to 4 carbon atoms and the alkoxy group having 1 to 4 carbon atoms is selected from the group consisting of, for example, a hydroxyl group, a carboxyl group, a cyano group, and a glycidyl group.
  • the substituent for the phenyl group is selected from the group consisting of, for example, a cyano group, a glycidyl group, a hydroxyl group, and a lower alkyl group having a hydroxyl group.
  • the substituent for the naphthyl group is selected from the group consisting of, for example, a cyano group, a glycidyl group, a hydroxyl group, a lower alkyl group having a hydroxyl group, a lower alkyl group having a glycidyl group, and a (meth) acryloyl group.
  • the substituent for the phenoxy group is selected from the group consisting of, for example, a hydroxyl group, a lower alkyl group having a glycidyl group, a (meth) acryloyl group, and a cyano group.
  • the substituent for the amide group is selected from the group consisting of, for example, a hydroxyl group, a glycidyl group, an isocyanuric group.
  • “Lower” may be, for example, a linear or branched chain having 1 to 4 carbon atoms. The substituent is not limited to these.
  • the substituent having an acryloyl group preferably has the following formula: (N represents an integer of 1 to 4, and m represents 0 or 1).
  • the substituent having a methacryloyl group is preferably of the following formula: (N represents an integer of 1 to 4, and m represents 0 or 1).
  • the polarizing plate provided with the flame retardant layer is excellent in that the optical performance such as the transmittance and the degree of polarization does not deteriorate even when compared with the polarizing plate before the provision of the flame retardant layer. Optical performance and excellent flame retardancy can be achieved.
  • PP-1 to PP-18 Specific examples (PP-1 to PP-18) of compounds having a 10-oxo-9-oxa-10-phosphaphenanthrene skeleton represented by the formula (1) are shown below.
  • M represents Cu, Ag, or Sb.
  • N represents an integer of 1 to 4)
  • the compound having a phosphazene skeleton is preferably a compound having a cyclotriphosphazene skeleton, and more preferably a compound having a 1,3,5,2,4,6-triazatriphosphorine skeleton.
  • the compound having a 1,3,5,2,4,6-triazatriphosphorine skeleton has the formula (2): It is preferable that it is a compound represented by these.
  • R 2 to R 7 are each independently, for example, hydrogen, an alkoxy group having 1 to 4 carbon atoms, an unsubstituted or substituted phenyl group, an unsubstituted or substituted phenoxy group, It is selected from the group consisting of a (meth) acryloyl group and a substituent having a (meth) acryloyl group.
  • the substituent for the phenyl group is selected from the group consisting of, for example, a cyano group, a glycidyl group, a hydroxyl group, and an alkyl group having a hydroxyl group.
  • the substituent for the phenoxy group is selected, for example, from the group consisting of a hydroxyl group, a lower alkyl group having a glycidyl group, a (meth) acryloyl group, and a cyano group, but is not limited thereto.
  • R 2 to R 7 may be the same or different. It is particularly preferred that R 2 to R 7 are each independently selected from the group consisting of the following Substituent Examples S-1 to S-4.
  • the substitution position of the (meth) acryloyl group is preferably at the terminal, but may be substituted as a side chain of the main chain in the substituent.
  • N represents an integer of 1 to 4, and m represents 0 or 1)
  • N represents an integer of 1 to 4, and m represents 0 or 1)
  • R 2 to R 7 are each independently a (meth) acryloyl group or a substituent having a (meth) acryloyl group, such as Substituent Example S-3 or Substituent Example S-4, the flame retardancy and hardness are An improved flame retardant layer is obtained, and a polarizing plate having the flame retardant layer has high flame retardancy and realizes optical performance such as transmittance almost equal to the case without the flame retardant layer. can do.
  • All of R 2 to R 7 may be a substituent having a (meth) acryloyl group or a (meth) acryloyl group, and 1 to 5 of R 2 to R 7 may be a (meth) acryloyl group or (meth ) It may be a substituent having an acryloyl group.
  • the polarizing plate provided with this flame retardant layer realizes better optical performance and superior flame retardancy than when a compound having a 10-oxo-9-oxa-10-phosphaphenanthrene skeleton is used. be able to.
  • (B) (Meth) acrylate compound that does not contain halogen and does not exhibit flame retardancy In some embodiments, the (meth) acrylate compound does not contain halogen and does not exhibit flame retardancy.
  • a well-known photopolymerization type or thermosetting type (meth) acrylate monomer compound can be used as the (meth) acrylate compound.
  • known (meth) acrylate monomer compounds include compounds having a (meth) acryloyl group as shown in, for example, “UV curing system” (published by General Technical Center, Kiyomi Kato, p. 259-303). However, it is not limited to these.
  • the (meth) acrylate compound which does not contain halogen and does not exhibit flame retardancy has one or more (meth) acryloyl groups, preferably 2 to 6.
  • a (meth) acrylate compound having two or more (meth) acryloyl groups in the resin composition the physical strength of the flame retardant layer is further improved, and the hardness and adhesion are improved, and the polarizing plate The durability of can be maintained more sufficiently.
  • an alkyl (meth) acrylate having 1 to 4 carbon atoms a polyacryl (meth) acrylate, preferably a pentaerythritol skeleton, neopentyl glycol (Meth) acrylate compounds having a skeleton, a trimethylolpropane skeleton, a bisphenol A skeleton, a bisphenol F skeleton, a dicyclopentadiene skeleton, an isocyanuric ring, particularly preferably a pentaerythritol skeleton, a neopentyl glycol skeleton, a trimethylolpropane skeleton, Examples include (meth) acrylate compounds having an isocyanuric ring.
  • the (meth) acrylate compound can be used alone or in combination of two or more.
  • the total content of the (meth) acrylate compound that does not contain halogen and does not exhibit flame retardancy in the resin composition is preferably 20 to 95% by mass, more preferably 25 to 95% by mass.
  • (meth) acrylate compound having two or more (meth) acryloyl groups is contained in the resin composition in an amount of 30 to 95% by mass, more preferably 40%. It is suitable to be contained in an amount of ⁇ 95% by mass, more preferably 50-95% by mass.
  • a (meth) acrylate compound having three or more (meth) acryloyl groups is contained in the resin composition.
  • the content is preferably 50 to 95% by mass, more preferably 60 to 95% by mass, and still more preferably 70 to 95% by mass.
  • a resin composition containing 30% by mass or more of a (meth) acrylate compound having two or more acryloyl groups a Japanese Industrial Standard JIS K 5600-5-4 as a layer generally called a hard coat layer A layer having a surface hardness of H or higher can be obtained, which is preferable.
  • the surface hardness of the flame retardant layer is preferably 2H or more, particularly preferably 3H or more.
  • the (meth) acrylate compound that does not contain halogen and does not exhibit flame retardancy is preferably a (meth) acrylate compound having a hydroxyl group in the molecule.
  • the adhesion between the flame retardant layer and the polarizing element can be further improved.
  • a cellulose-based film, particularly triacetate cellulose (TAC) or other transparent acetylcellulose-based film is used as a protective layer of the polarizing element, This is particularly preferable because it can improve the adhesion.
  • the content of the hydroxyl group-containing (meth) acrylate compound is, for example, 25 to 90% by mass, preferably 30 to 80% by mass, more preferably 40 to 70% by mass, and further preferably 45 to 65% by mass in the resin composition. It is.
  • Examples of the (meth) acrylate compound having a hydroxyl group in the molecule include a reaction product of trimethylolpropane triglycidyl ether and acrylic acid [DENACOL DA-321, Nagase Sangyo Co., Ltd.], triglycerol diacrylate [epoxy ester] 80MFA, manufactured by Kyoeisha Yushi Co., Ltd.], reaction product of propylene glycol diglycidyl ether and acrylic acid [DENACOL DA-911, manufactured by Nagase Sangyo Co., Ltd.], reaction product of diglycidyl phthalate and acrylic acid [DENACOL DA-721 (manufactured by Nagase Sangyo Co., Ltd.), pentaerythritol triacrylate [KAYARAD PET-30 manufactured by Nippon Kayaku Co., Ltd.], reaction product of 1,6-hexanediol diglycidyl ether and acrylic acid [KAYAR D-167 manufactured
  • reaction product of butyl glycidyl ether and acrylic acid [DENACOL DA-151, manufactured by Nagase Sangyo Co., Ltd.], butanediol monoacrylate [SR-676, manufactured by Sartomer Co., Ltd.], and the like.
  • pentaerythritol triacrylate reaction product of 1,6-hexanediol diglycidyl ether and acrylic acid, reaction of 2-hydroxyethyl methacrylate, 2-hydroxyethyl acrylate, bisphenol A diglycidyl ether and acrylic acid
  • examples of the product include, but are not limited to.
  • pentaerythritol triacrylate As the (meth) acrylate compound having a hydroxyl group in the molecule, pentaerythritol triacrylate (KAYARAD PET-30 manufactured by Nippon Kayaku Co., Ltd.) is preferable because it most improves the wet heat durability of the polarizing plate.
  • Ratio of halogen-free flame retardant having (meth) acryloyl group or halogen-free flame retardant not having (meth) acryloyl group and (meth) acrylate compound which is halogen-free and does not exhibit flame retardancy Is preferably a mass ratio of 5:95 to 80:20.
  • the blending ratio is within this range, there is an effect that high transparency and smooth film forming property can be realized while having flame retardancy.
  • the halogen-free flame retardant having a (meth) acryloyl group has two or more (meth) acryloyl groups
  • the blending ratio is a mass ratio of 10:88 to 75:23. It is preferable in order to realize high hardness, adhesion, and high durability along with the properties.
  • the range of 25:73 to 68:30 is preferable because flame retardancy and transparency are particularly high and durability is improved.
  • the resin composition may further contain a polymerization initiator.
  • the polymerization initiator is selected according to the type of polymerizable monomer such as the halogen-free flame retardant having the (meth) acryloyl group and the (meth) acrylate compound which does not contain halogen and does not exhibit flame retardancy.
  • an ultraviolet polymerization initiator is preferred.
  • the ultraviolet polymerization initiator include 2-methyl-1- [4- (methylthio) phenyl] -2-morpholinopropane-1 (IRGACURE 907 manufactured by Ciba Specialty Chemicals), 1-hydroxycyclohexyl phenyl ketone (Ciba Specialty).
  • the ultraviolet polymerization initiator is 2-methyl-1- [4- (methylthio) phenyl] -2-morpholinopropane-1 (IRGACURE 907 manufactured by Ciba Specialty Chemicals), 1-hydroxycyclohexyl phenyl ketone (Ciba Specialty). IRGACURE 184 manufactured by Tea Chemicals) or 2,2-dimethoxy-2-phenylacetophenone (IRGACURE 651 manufactured by Ciba Specialty Chemicals). These photopolymerization initiators can be used singly or in combination of a plurality of them at an arbitrary blending ratio.
  • an auxiliary agent can be used in combination to promote the photopolymerization reaction.
  • the auxiliary agent for example, triethanolamine, methyldiethanolamine, triisopropanolamine, n-butylamine, N-methyldiethanolamine, diethylaminoethyl methacrylate, Michler's ketone, 4,4′-diethylaminophenone, ethyl 4-dimethylaminobenzoate, Examples thereof include amine compounds such as 4-dimethylaminobenzoic acid (nbutoxy) ethyl and isoamyl 4-dimethylaminobenzoate.
  • the addition amount of the photopolymerization initiator and the auxiliary agent is preferably used in a range in which the optical performance and flame retardancy of the polarizing plate do not decrease, and the amount of the (meth) acrylate monomer in the resin composition is 100 parts by mass. On the other hand, it is preferably 0.5 to 12 parts by mass, more preferably 2 to 10 parts by mass.
  • the auxiliary agent is preferably added in a mass of 0.5 to 2 times the photopolymerization initiator.
  • the resin composition may further contain a leveling agent.
  • a leveling agent By containing a leveling agent, when the resin composition is applied onto a protective layer or polarizing element as a substrate, the wettability on the substrate and the surface property of the formed resin composition layer are improved. Can do.
  • various compounds such as silicon-based, fluorine-based, polyether-based, acrylic acid copolymer-based, and titanate-based compounds can be used.
  • the leveling agent is added in an amount of about 0.0001 to 10 parts by mass, more preferably about 0.1 to 5 parts by mass with respect to 100 parts by mass of the (meth) acrylate monomer in the resin composition.
  • the resin composition can further contain a crosslinking agent.
  • a crosslinking agent By containing a crosslinking agent, the adhesiveness with the board
  • the type of the crosslinking agent various compounds such as isocyanate, boron, and titanate can be used.
  • the addition amount of the crosslinking agent is preferably about 0.0001 to 20 parts by mass, more preferably about 0.1 to 10 parts by mass with respect to 100 parts by mass of the (meth) acrylate monomer in the resin composition.
  • the polymerizable monomer in the resin composition is a thermosetting type
  • a polymerization initiator, a crosslinking agent and / or an initiation catalyst can be further contained in the resin composition.
  • the type of the crosslinking agent various known compounds such as isocyanate, boron, and titanate can be used.
  • the addition amount of the crosslinking agent is preferably about 0.1 to 20 parts by mass, more preferably about 1 to 10 parts by mass with respect to 100 parts by mass of the (meth) acrylate monomer in the resin composition.
  • the flame retardant layer (B) is a flame retardant layer made of a cured product of a resin composition containing a predetermined amount of a halogen-free flame retardant having one or more (meth) acryloyl groups.
  • the content of the halogen-free flame retardant having one or more (meth) acryloyl groups in the resin composition is 10 to 99.9% by mass, preferably 15 to 75% by mass, more preferably 25 to 70% by mass. Particularly preferred is 35 to 65% by mass.
  • the performance of the flame retardant layer can be improved, and it has high flame retardancy and maintains almost the same optical performance as a polarizing element alone.
  • the production of the polarizing plate can be realized.
  • the polarizing plate provided with the flame retardant layer is excellent in that the optical performance such as the transmittance and the degree of polarization does not deteriorate even when compared with the polarizing plate before the provision of the flame retardant layer. Optical performance and excellent flame retardancy can be achieved.
  • halogen-free flame retardant having one or more (meth) acryloyl groups an organic phosphorus compound that is a part of the meta (acrylate) described for the flame retardant layer (A) can be used, and preferably a phosphorous compound. It is a compound having a faphenanthrene skeleton or a phosphazene skeleton.
  • the compound having a phosphaphenanthrene skeleton, the compound having a phosphazene skeleton, and the compound having a cyclotriphosphazene skeleton may be used singly or in a combination of two or more.
  • the flame retardant having a phosphaphenanthrene skeleton is preferably a compound having a 10-oxo-9-oxa-10-phosphaphenanthrene skeleton.
  • a compound having a 10-oxo-9-oxa-10-phosphaphenanthrene skeleton has the formula (1): It is preferable that it is a compound represented by these.
  • R 1 is preferably a substituent having a (meth) acryloyl group or a (meth) acryloyl group.
  • the substitution position of the (meth) acryloyl group is preferably at the terminal, but may be substituted with a side chain in the main chain of the substituent.
  • the substituent having an acryloyl group preferably has the following formula: (N represents an integer of 1 to 4, and m represents 0 or 1).
  • the substituent having a methacryloyl group is preferably of the following formula: (N represents an integer of 1 to 4, and m represents 0 or 1).
  • Specific examples of the compound represented by the formula (1) include compound examples PP-1 to PP-18, preferably compound example PP-17 and compound example PP-18.
  • the compound having a phosphazene skeleton is preferably a compound having a cyclotriphosphazene skeleton, and more preferably a compound having a 1,3,5,2,4,6-triazatriphosphorine skeleton.
  • the compound having a 1,3,5,2,4,6-triazatriphosphorine skeleton has the formula (2): It is preferable that it is a compound represented by these.
  • R 2 to R 7 may be the same or different and are each independently a substituent having, for example, a (meth) acryloyl group or a (meth) acryloyl group.
  • the substitution position of the (meth) acryloyl group is preferably at the terminal, but may be substituted as a side chain in the main chain.
  • the above-described substituent examples S-1 to S-4 are preferable, and substituent example S-3 and substituent example S-4 are particularly preferable.
  • the resin composition for preparation of the flame retardant layer (B) is the same as that described above for the flame retardant layer (A) with the polymerization initiator, auxiliary agent, crosslinking agent, and / or initiation catalyst. It can be further contained in a content of about.
  • the flame retardant layers (A) and (B) and the later-described (C) can have the functions of various layers constituting a general polarizing plate.
  • the flame retardant layer can also be a layer generally called a hard coat layer, or a monomer composition containing an acrylic acid-based alkyl ester described in Japanese Patent No. 3410835 and Japanese Patent No. 3645005. It may also be an adhesive layer made of the (co) polymer.
  • the flame retardant layer can also be a layer that has other functions, thereby reducing the number of laminated films constituting the polarizing plate and increasing the flame resistance due to the increase in the number of laminated films. Can be suppressed.
  • the flame retardant layer (C) is a layer containing a compound having a phosphaphenanthrene skeleton and / or a compound having a phosphazene skeleton.
  • the flame retardant layer may be a layer having only a function of imparting flame retardancy to the polarizing plate, or may be a layer having the function of any layer constituting the flame retardant polarizing plate.
  • the flame retardant layer is preferably a layer that also functions as a layer selected from the group consisting of an adhesive layer, an adhesive layer, and a hard coat layer.
  • the flame retardant layer can also be a layer that has other functions, thereby reducing the number of laminated films constituting the polarizing plate and increasing the flame resistance due to the increase in the number of laminated films. Can be suppressed.
  • the flame retardant layer is a layer that also functions as another layer constituting the polarizing plate, for example, an adhesive layer, an adhesive layer, or a hard coat layer, it has been used so far to produce the layer. It can be produced by adding a compound having a phosphaphenanthrene skeleton and / or a compound having a phosphazene skeleton to a resin composition containing a monomer composition as a base. Thereby, the flame retardance which was excellent with only the addition of few manufacturing processes can be given to a polarizing plate.
  • a resin composition containing a compound having a phosphaphenanthrene skeleton and / or a phosphazene skeleton as long as the optical performance and flame retardancy of the polarizing plate are not impaired, it is known for the production of each layer constituting the polarizing plate.
  • a resin composition preferably a resin composition containing an acrylic acid monomer can be used.
  • a flame-retardant layer is a layer suitable also as a hard-coat layer and the case where it is a layer suitable also as an adhesion layer are explained in full detail.
  • C1 When suitable for a hard coat layer As a flame retardant layer suitable for a hard coat layer, 5 to 80% by mass of a compound having a phosphaphenanthrene skeleton and / or a compound having a phosphazene skeleton has the phosphaphenanthrene skeleton.
  • the resin composition can optionally further contain other components such as a polymerization initiator, an auxiliary agent, a crosslinking agent, and a leveling agent.
  • A Compound having phosphaphenanthrene skeleton and compound having phosphazene skeleton
  • Compound having phosphaphenanthrene skeleton is preferably [a flame retardant layer (A)]
  • A) The “compound having a phosphaphenanthrene skeleton” described for the halogen-free flame retardant.
  • (A2) Compound having phosphazene skeleton
  • the compound having a phosphazene skeleton is preferable for (a) halogen-free flame retardant of [Flame retardant layer (A)] in order to particularly improve the flame retardant function.
  • This is the “compound having a phosphazene skeleton” described.
  • the above compounds having a phosphaphenanthrene skeleton and / or a compound having a phosphazene skeleton may be used singly or in a combination of two or more at any ratio.
  • the compound having a phosphaphenanthrene skeleton and / or the compound having a phosphazene skeleton does not have a (meth) acryloyl group
  • the amount is, for example, 5 to 80% by mass, preferably 15 to 75% by mass, more preferably 25 to 70% by mass, and further preferably 35 to 70% by mass.
  • the content of the compound having a phosphaphenanthrene skeleton and / or the compound having a phosphazene skeleton in the resin composition is: For example, it is 10 to 99% by mass, preferably 15 to 80% by mass, more preferably 25 to 70% by mass, and further preferably 35 to 65% by mass.
  • the adhesiveness to the base material is maintained while maintaining high flame retardancy. , Has the effect of imparting durability and flexibility.
  • (B) (Meth) acrylate compound The (meth) acrylate compound is a compound different from the compound having the phosphaphenanthrene skeleton and the compound having the phosphazene skeleton.
  • the “(meth) acrylate compound that does not contain halogen and does not exhibit flame retardancy” described for (a) halogen-free flame retardant in [Flame-retardant layer (A)] can be used.
  • the total content of the (meth) acrylate compound in the resin composition is, for example, 1 to 95% by mass, preferably 20 to 95% by mass, and more preferably 20 to 85% by mass.
  • the (meth) acrylate compound having two or more (meth) acryloyl groups is 20 to 95% by mass, more preferably 30% in the resin composition. It is preferable to contain it in an amount of ⁇ 85 mass%, more preferably 20-95 mass%.
  • a (meth) acrylate compound having three or more (meth) acryloyl groups is contained in the resin composition.
  • the content is preferably 20 to 95% by mass, more preferably 25 to 80% by mass, and still more preferably 35 to 65% by mass.
  • a resin composition containing 30% by mass or more of a (meth) acrylate compound having two or more acryloyl groups a Japanese Industrial Standard JIS K 5600-5-4 as a layer generally called a hard coat layer A layer having a surface hardness of H or higher can be obtained, which is preferable.
  • the surface hardness of the flame retardant layer is preferably 2H or more, particularly preferably 3H or more.
  • part or all of the (meth) acrylate compound is preferably a (meth) acrylate compound having a hydroxyl group in the molecule.
  • the adhesion of the flame retardant layer to the polarizing element can be further improved.
  • a cellulose-based film particularly triacetate cellulose (TAC) or other transparent acetylcellulose-based film is used as a protective layer of the polarizing element, This is particularly preferable because it can improve the adhesion.
  • TAC triacetate cellulose
  • the content of the hydroxyl group-containing (meth) acrylate compound is, for example, 20 to 90% by mass, preferably 30 to 80% by mass, more preferably 40 to 70% by mass, and further preferably 45 to 65% by mass in the resin composition. It is.
  • Examples of the (meth) acrylate compound having a hydroxyl group in the molecule include those described for (a) halogen-free flame retardant of [Flame Retardant Layer (A)].
  • the compounding ratio of the compound having a phosphaphenanthrene skeleton and / or the compound having a phosphazene skeleton and the (meth) acrylate compound that does not contain halogen and does not exhibit flame retardancy is a mass ratio of 5:94 to 80:19. Preferably there is.
  • the blending ratio is within this range, there is an effect of improving flame retardancy, hardness, and durability.
  • the compound having a phosphaphenanthrene skeleton and / or the compound having a phosphazene skeleton has two or more (meth) acryloyl groups, it is difficult for the mixing ratio to be a mass ratio of 10:88 to 75:28. It is preferable because the flammability can be further improved and the hardness and durability are further improved. More preferably, it is 20:78 to 70:28, still more preferably 30:68 to 65:33, and particularly preferably 35:63 to 65:33.
  • the resin composition may further contain the polymerization initiator described for (a) the halogen-free flame retardant of [Flame Retardant Layer (A)].
  • the resin composition may further contain the leveling agent described for (a) halogen-free flame retardant of [Flame Retardant Layer (A)].
  • the resin composition may further contain the crosslinking agent described for (a) halogen-free flame retardant of [Flame retardant layer (A)].
  • the polymerizable monomer in the resin composition is of a thermosetting type
  • a catalyst can be further contained in the resin composition.
  • the flame retardant layers (A), (B), and (C) for example, a coating liquid obtained by diluting the resin composition as it is or using a suitable solvent.
  • a suitable solvent examples include applying to a protective layer or a polarizing element, then removing the solvent by heating or the like, and curing by heating or irradiating with ultraviolet rays.
  • the solvent for dilution is not particularly limited as long as it is excellent in solubility of the resin composition and wettability on the substrate at the time of application and does not cause deterioration in surface properties.
  • Examples of the solvent for dilution include water, aromatic hydrocarbons such as toluene and xylene, ethers such as anisole, dioxane and tetrahydrofuran, methyl isobutyl ketone, methyl ethyl ketone, cyclohexanone, cyclopentanone, 2-pentanone and 3-pentanone. , Ketones such as 2-hexanone, 3-hexanone, 2-heptanone, 3-heptanone, 4-heptanone, 2,6-dimethyl-4-heptanone, n-butanol, 2-butanol, cyclohexanol, isopropyl alcohol, etc.
  • aromatic hydrocarbons such as toluene and xylene
  • ethers such as anisole, dioxane and tetrahydrofuran
  • methyl isobutyl ketone methyl ethyl ketone
  • Alcohols, cellosolves such as methyl cellosolve, methyl cellosolve acetate, ethyl acetate, butyl acetate, methyl lactate, propylene glycol monomethyl ether acetate, propylene glycol ethyl ether acetate, methoxyethyl acetate Esters such as succinate San ethoxyethyl, dimethyl sulfoxide, acetonitrile, N, including but N- dimethylacetamide dimethylformamide without limitation. Toluene, cyclopentanone, and ethyl acetate are preferable. Further, the solvent may be one kind alone or a mixture of two or more kinds.
  • the concentration of the total solid content in the coating solution varies depending on the solvent solubility, the wettability on the substrate to be coated, the thickness after coating, etc., but is preferably 5 to 95% by mass, more preferably 10 to 80% by mass. % Is good.
  • a resin layer may be provided by coating on a substrate of a layer such as a protective layer, a protective film, or a polarizing element.
  • a method in which a layer that has been applied to another film in advance and cured is transferred or laminated onto a substrate such as a protective layer or a polarizing element may be used.
  • a layer may be provided by a method such as coating directly on a polyvinyl alcohol film on which dichroic dye and boric acid are adsorbed.
  • the cured layer is a protective layer, a substrate such as a polarizing element, or dichroism
  • a method of transferring or laminating a dye on a polyvinyl alcohol film to which the dye is adsorbed and oriented may be used.
  • the method of providing the adhesive layer at the same time as the method of providing the layer is also efficient, and furthermore, the polarizing plate having the flame retardant layer can be most easily prepared when the adhesive layer itself is a resin composition.
  • the application method is not particularly limited, and examples thereof include a spin coating method, a wire bar coating method, a gravure coating method, a micro gravure coating method, a calendar coating method, a spray coating method, and a meniscus coating method.
  • the cured layer obtained by curing the resin composition is sufficiently polymerized by heating or ultraviolet irradiation and has as little unreacted content as possible.
  • the degree is preferably adjusted so that the unreacted acrylate compound in the cured resin composition is 0 to 5% by mass, more preferably 0 to 3% by mass, and still more preferably 0 to 1% by mass.
  • the method include curing by changing the atmosphere at the time of ultraviolet irradiation, such as irradiation with ultraviolet rays, or in an inert gas such as nitrogen.
  • the optimization of the thickness of the resin layer is the simplest because it can be carried out only by changing the resin concentration and the resin coating amount.
  • the thickness of the flame retardant layer obtained by curing the resin composition is 0.1 to 100 ⁇ m, preferably 0.5 to 10 ⁇ m, more preferably 1 to 8 ⁇ m, and further preferably 2 to 6 ⁇ m. If it is thicker than 100 ⁇ m, the residual unreacted monomer increases, the wet heat durability is insufficient, and the polarizing plate turns red in the dry heat durability test, which is not suitable. On the other hand, a layer thinner than 0.1 ⁇ m does not lead to improvement in wet heat durability.
  • the amount of UV irradiation varies depending on the type of acrylate compound, the type and addition amount of the photopolymerization initiator, and the film thickness, but is preferably about 100 to 1500 mJ / cm 2 , for example.
  • the obtained flame-retardant layer is transparent even if it is treated with an alkaline solution. Specifically, it is one index that there is no white turbidity after being treated with an alkaline aqueous solution having a pH of 11 or more at 40 ° C. for 10 minutes or more.
  • the wavelength is 550 nm.
  • the light transmittance in is preferably 85% or more, and more preferably 90% or more.
  • the flame retardant layer hydrophilic by treating the flame retardant layer obtained by curing the resin composition with an alkaline aqueous solution because the adhesion to the polyvinyl alcohol film is improved.
  • the contact angle when 10 ⁇ l of water is dropped is preferably 60 ° or less, more preferably 50 ° or less, and still more preferably 40 ° or less.
  • the flame retardant layer is bonded to the polarizing element, it is preferable to use a flame retardant layer that is treated with an aqueous alkali solution after curing, neutralized with water or an acidic aqueous solution, and then dried.
  • the flame retardant layer suitable for the adhesive layer is obtained by polymerizing or copolymerizing a pressure-sensitive adhesive resin composition containing a compound having a phosphaphenanthrene skeleton and / or a compound having a phosphazene skeleton. Can be formed. Including 5 to 80% by mass of a compound having a phosphaphenanthrene skeleton and / or a compound having a phosphazene skeleton in the adhesive resin composition or in a layer obtained thereby imparts flame retardancy. However, it is good because of its high transparency and good adhesion. More preferably, it is 10 to 70% by mass, more preferably 12 to 50% by mass, particularly preferably 14 to 35% by mass, in order to maintain high durability while maintaining high flame retardancy. preferable.
  • (C1) the same kind of compound as described above for the case suitable for the hard coat layer, the resin composition for the adhesive layer with the same content ( Hereinafter, it is also referred to as “resin composition for pressure-sensitive adhesive layer” or “pressure-sensitive adhesive resin composition”), or has a phosphaphenanthrene skeleton as a copolymer component contained in the pressure-sensitive adhesive resin composition.
  • a (meth) acrylate or a (meth) acrylate compound having a phosphazene skeleton may be contained.
  • the pressure-sensitive adhesive resin composition preferably contains a (meth) acrylate compound, particularly an acrylic acid alkyl ester as a tackifier.
  • the pressure-sensitive adhesive resin composition comprises a polymerizable monomer having a hydroxyl group, a polymerizable monomer having an amide group, a polymerizable monomer having a carboxyl group, and / or a polymerizable monomer having no functional group, in addition to an acrylic acid alkyl ester. Additional monomer components such as can be included as desired.
  • the pressure-sensitive adhesive resin composition preferably contains at least two or more acrylic acid alkyl esters or at least one or more acrylic acid allyl esters and one or more additional monomer components.
  • Preferred acrylic acid alkyl esters include, for example, methyl (meth) acrylate, ethyl (meth) acrylate, isopropyl (meth) acrylate, n-propyl (meth) acrylate, isobutyl (meth) acrylate, (meth) One or a combination of two or more selected from the group consisting of (meth) acrylic acid C1-12 alkyl esters such as n-butyl acrylate, t-butyl (meth) acrylate, and dodecyl (meth) acrylate It is.
  • the acrylic acid alkyl ester is one kind selected from the group consisting of n-butyl (meth) acrylate, t-butyl (meth) acrylate, and methyl (meth) acrylate, or two or more kinds. It is a combination.
  • the acrylic acid alkyl ester is a combination of n-butyl (meth) acrylate and t-butyl (meth) acrylate, or n-butyl (meth) acrylate, t-butyl (meth) acrylate, and ( A combination of (meth) methyl acrylate is preferable because durability is particularly good.
  • “(meth) acrylic acid” means acrylic acid and / or methacrylic acid.
  • the content of the monomer based on the acrylic acid alkyl ester in the pressure-sensitive adhesive resin composition is preferably 50 to 100% by mass, more preferably 70 to 95% by mass.
  • the solubility of the component having the phosphaphenanthrene skeleton or the phosphazene skeleton and / or the (meth) acrylate compound thereof is increased, and the permeation due to precipitation of the compound is performed. Reduction in rate is suppressed.
  • the adhesive layer obtained from the adhesive resin composition deteriorates, for example, foaming and generation of micro defects, a component that is a phosphaphenanthrene skeleton or phosphazene skeleton, or / And lowering of adhesion to glass and film due to precipitation of the (meth) acrylate compound and transparency are unlikely to occur, and discoloration, white turbidity, and physical properties of the optical film provided with the adhesive layer It is possible to reduce deterioration such as mechanical destruction.
  • Examples of the polymerizable monomer having a preferred hydroxyl group contained in the adhesive resin composition include 2-hydroxyethyl acrylate, 2-hydroxyethyl methacrylate, 2-hydroxypropyl acrylate, 2-hydroxypropyl methacrylate, 3-chloro-2- Examples include hydroxy C1-5 alkyl (meth) acrylates such as hydroxypropyl acrylate and 3-chloro-2-hydroxypropyl methacrylate, diethylene glycol monomethacrylate and diethylene glycol (meth) acrylate such as diethylene glycol monomethacrylate, and glycidyl methacrylate and allyl. Examples thereof include glycidyl ether.
  • the content of the polymerizable monomer having a hydroxyl group in the pressure-sensitive adhesive resin composition is preferably 0.5 to 7 parts by mass, more preferably 0.8 to 4.3 parts per 100 parts by mass of the acrylic acid alkyl ester. Part by mass.
  • Preferred examples of the polymerizable monomer having an amide group used in the pressure-sensitive adhesive resin composition include N, N-dimethylaminopropylacrylamide, N, N-dimethylacrylamide, N, N-diethylacrylamide, acryloylmorpholine, and N-isopropylacrylamide.
  • Acrylamide monomers such as N-methylolacrylamide and acrylamide.
  • the content of the polymerizable monomer having an amide group in the pressure-sensitive adhesive resin composition is preferably 0.5 to 29 parts by mass, more preferably 3 to 21 parts by mass with respect to 100 parts by mass of the acrylic acid alkyl ester. is there.
  • the transparency of the pressure-sensitive adhesive layer obtained from the pressure-sensitive adhesive resin composition is increased, and the pressure-sensitive adhesive layer and the flame-retardant polarizing plate provided with the high-temperature, high humidity, and high strength The durability against light irradiation can be further improved.
  • Examples of preferable polymerizable monomers having a carboxyl group contained in the pressure-sensitive adhesive resin composition include acrylic acid, methacrylic acid, maleic acid, and itaconic acid.
  • the polymerizable monomer having a carboxyl group is contained in the monomer composition in combination with the polymerizable monomer having an amide group, and does not interfere with each other's compatibility, and the transparency of the adhesive layer made of the adhesive resin composition Is preferable because it does not lower the thickness.
  • the content of the polymerizable monomer having a carboxyl group in the adhesive resin composition is preferably 0.5 to 7 parts by mass, more preferably 1 to 4.3 parts by mass with respect to 100 parts by mass of the acrylic acid alkyl ester. It is.
  • a polymerizable monomer having a carboxyl group in the above range, it is possible to increase the concentration of the ultraviolet absorber while suppressing a decrease in the transmittance of the adhesive layer, and to provide high-temperature, high-humidity, and high-intensity light. Even under irradiation conditions, it is possible to further enhance the effect of suppressing the deterioration of the adhesive layer, for example, the deterioration of transparency and adhesion over a long period of time.
  • Examples of the polymerizable monomer having no preferred functional group contained in the pressure-sensitive adhesive resin composition include vinyl acetate, acrylonitrile, and styrene.
  • the content of the polymerizable monomer having no functional group in the monomer composition is preferably 0 to 43 parts by mass with respect to 100 parts by mass of the acrylic acid alkyl ester.
  • the pressure-sensitive adhesive resin composition comprises 100 parts by mass of an acrylic acid alkyl ester, 0.5 to 7 parts by mass of a polymerizable monomer having a hydroxyl group, and 0.5 to 29 parts by mass of a polymerizable monomer having an amide group. It is particularly preferred that the flame retardant polarizing plate can further enhance the durability of the flame retardant polarizing plate.
  • the pressure-sensitive adhesive resin composition further contains 0.5 to 7 parts by weight of a polymerizable monomer having a carboxyl group, thereby reducing the transmittance of the pressure-sensitive adhesive layer even when the concentration of the phosphaphenanthrene compound and / or phosphazene compound is higher.
  • a pressure-sensitive adhesive resin composition that is capable of forming a pressure-sensitive adhesive layer that is suppressed and that is further prevented from deteriorating under high temperature, high humidity, and high-intensity light irradiation conditions, for example, deterioration in transparency and adhesion over a long period of time. Can be obtained.
  • a monomer component contained in the pressure-sensitive adhesive resin composition a monomer composition containing an acrylic acid alkyl ester described in Japanese Patent No. 3410835 and Japanese Patent No. 3645005 may be used.
  • the pressure-sensitive adhesive layer can be produced by dissolving the pressure-sensitive adhesive resin composition in an organic solvent and performing radical copolymerization in the organic solvent by a general method.
  • organic solvent used for polymerization include aromatic hydrocarbons such as toluene and xylene, esters such as ethyl acetate and butyl acetate, aliphatic alcohols such as n-propyl alcohol and isopropyl alcohol, and methyl ethyl ketone and Examples thereof include ketones such as methyl isobutyl ketone.
  • polymerization catalyst used for radical polymerization examples include azobisisobutyronitrile, benzoyl peroxide, di-t-butyl peroxide, cumene hydroperoxide, and the like, which are usual polymerization catalysts.
  • the copolymer obtained from the pressure-sensitive adhesive resin composition, or the composition thereof includes monomer units based on the respective monomers contained in the pressure-sensitive adhesive resin composition, and the content of each monomer unit is determined based on each monomer in the monomer composition. It corresponds to the content of.
  • the acrylic copolymer resin preferably contains 50 to 100% by mass of monomer units based on acrylic acid alkyl ester, and optionally has a hydroxyl group based on 100 parts by mass of monomer units based on acrylic acid alkyl ester.
  • the monomer unit is further contained in an amount of 0.5 to 7 parts by mass, and / or the monomer unit based on a polymerizable monomer having no functional group is preferably contained in an amount of 0 to 43 parts by mass.
  • the cured product of the pressure-sensitive adhesive resin composition has a glass transition temperature (hereinafter abbreviated as Tg) of ⁇ 20 ° C. or lower, preferably ⁇ 30 ° C. to ⁇ 60 ° C., and a weight average molecular weight of 500,000-2. , 000,000, preferably 700,000 to 1,600,000.
  • Tg glass transition temperature
  • the weight average molecular weight is less than 500,000, the heat resistance may be insufficient, and if it exceeds 2,000,000, the adhesion tends to be insufficient, and peeling or the like is likely to occur. is there.
  • ⁇ Film thickness When the film thickness of the flame retardant layer is between 0.1 and 100 ⁇ m, the flame retardancy is exhibited, but when it is a hard coat layer, for example, 0.5 to 20 ⁇ m, preferably 0.5 to 15 ⁇ m. More preferably, the thickness is 1 to 10 ⁇ m.
  • an adhesive layer for example, 5 to 100 ⁇ m, preferably 8 to 50 ⁇ m, more preferably 10 to 40 ⁇ m, and most preferably 15 to 30 ⁇ m.
  • such a flame retardant layer may be laminated with another adhesive layer, or a flame retardant layer may be further laminated to use as a single adhesive layer although it is a multilayer.
  • the flame retardant layer is provided as any layer in the polarizing plate, flame retardancy is exhibited, but particularly on the surface layer side of the polarizing element, for example, a layer provided on the surface, an adhesive layer, or an adhesive layer. Any one of the layers provided on the surface layer can provide not only “not easily burn” but also "not burn” performance, protect the polarizing element, maintain its optical properties, and also as a polarizing plate It is preferable because it does not burn.
  • the flame retardant polarizing plate includes a polarizing element and a flame retardant layer provided on one side or both sides of the polarizing element.
  • the flame retardant polarizing plate optionally includes additional layers such as a protective layer, a pressure-sensitive adhesive layer, a retardation film, an adhesive layer, a surface scratch prevention layer, and an antiglare layer. Further layers such as a protective layer, a pressure-sensitive adhesive layer, and a retardation film may be disposed between the polarizing element and the flame-retardant layer.
  • the above-described flame retardant layer (A), (B), or (C) is used as the flame retardant layer.
  • the flame retardant layer of one aspect may be provided on one surface and the flame retardant layer of another aspect may be provided on the other surface.
  • the polarizing element As the polarizing element, a commonly used one can be used, and preferably a flammable polarizing element can be used.
  • the polarizing element is, for example, a dichroic dye such as iodine or a dichroic dye on a film formed from a polyvinyl alcohol resin such as polyvinyl alcohol, polyvinyl formal, polyvinyl acetal, saponified ethylene-vinyl acetate copolymer, etc. Is a film imparted with polarization by stretching with boric acid or the like as a crosslinking agent.
  • polarizing element examples include those described in JP-A-8-190016, JP-A-11-119023, JP-A-11-218611, and Japanese Patent No. 4360100. It is done. Further, a polarizing element having a polyene structure by dehydration reaction of polyvinyl alcohol as disclosed in Japanese Patent No. 3001984 and Japanese Patent No. 4269939, and Japanese Patent No. 4275691 in which unevenness is provided on a resin substrate to form a polarizing element, and Examples thereof include a polarizing element described in Japanese Patent No. 4275692.
  • plastic film having excellent transparency, mechanical strength, thermal stability, moisture shielding properties, and the like is further provided as a protective layer on one or both surfaces of the polarizing element.
  • plastics having excellent transparency, mechanical strength, thermal stability, moisture shielding properties, etc. include polyester resins, cellulose resins, acetate resins, polyethersulfone resins, polycarbonate resins, polyamide resins, polyimides.
  • Thermoplastic resins such as epoxy resins, polyolefin resins, and acrylic resins, and thermosetting resins and ultraviolet curable resins such as acrylic, urethane, acrylic urethane, epoxy, and silicone resins. .
  • the polyolefin-based resin may be a non-crystalline polyolefin-based resin having a cyclic polyolefin polymerized unit such as norbornene or a polycyclic norbornene-based monomer.
  • the cellulose protective layer may be provided in the single side
  • a cellulose film in particular, triacetyl cellulose is generally used.
  • the flame retardant polarizing plate may further include, for example, a hard coat layer such as an adhesive layer, an adhesive layer, a surface scratch prevention layer and an antiglare layer, and / or a retardation film.
  • a hard coat layer such as an adhesive layer, an adhesive layer, a surface scratch prevention layer and an antiglare layer, and / or a retardation film.
  • the thing used for can be used.
  • the retardation film a film provided with retardation by stretching a film produced from a resin such as polyvinyl alcohol, polycarbonate, cycloolefin, or the like is preferably used. It may be a film coated with a substance or a film having the layer.
  • the retardation film is preferably laminated on a polarizing element or a protective layer.
  • the retardation film may be provided on a layer such as a flame retardant layer or a pressure-sensitive adhesive layer.
  • the pressure-sensitive adhesive layer is a general pressure-sensitive adhesive, preferably an acrylic pressure-sensitive adhesive, for example, an acrylic (co) obtained from an acrylic acid-based alkyl ester monomer described in Japanese Patent No. 3410835 and Japanese Patent No. 364005. It is formed of a polymer resin or a silicone-based pressure-sensitive adhesive.
  • the adhesive layer may be disposed so as to be in direct contact with the polarizing element or the retardation plate, or may be disposed on the polarizing element or the retardation plate via another layer.
  • the adhesive layer is preferably provided on the outermost layer on one side or both sides of the flame-retardant polarizing plate.
  • the flame retardant layer can impart flame retardancy regardless of the position, but the flame retardant layer is exposed to the environment exposure surface side of the polarizing element and / or exposed to the light source.
  • a layer provided on the surface side through a protective layer (protective film) and other layers is preferable, and such a layer is provided on both the environment exposure surface side and the light source exposure surface side of the polarizing element. It is more preferable.
  • the position of the flame retardant layer is preferably the outermost layer on the environment exposed surface side and / or the light source exposed surface side.
  • An environmentally exposed surface or a light source exposed surface is a surface that is directly exposed to external factors such as light, heat, humidity, impact, and fire.
  • a polarizing plate is generally bonded to both sides of a liquid crystal cell, but in a polarizing plate bonded to an observer side of a liquid crystal cell, a polarizing element It represents that a flame retardant layer is provided on the viewer side, that is, provided as a layer disposed on the environment exposure surface side of the polarizing element.
  • the light source exposed surface side refers to the provision of a flame retardant layer on the light source side, commonly called the backlight side, when polarizing plates are bonded to both sides of the liquid crystal cell.
  • the backlight side When irradiating a board, it refers to providing a flame retardant layer on the side irradiated with light.
  • the temperature increases due to the intensity of the light, and it burns and develops into a fire. It is known to do. It is possible to prevent the phenomenon of burning or spreading of fire due to factors such as light from the exposed surface of the light source, heat, and fire.
  • the flame retardant layer is a layer provided on the exposed surface side of the environment, for example, an adhesive layer and / or a hard coat layer.
  • the “flammable” performance non-flammable) Property
  • the flame retardant polarizing plate for example, FR layer / protective layer / polarizing element / protective layer, FR layer / protective layer / polarizing element / protective layer / FR layer, FR layer / polarizing element / FR layer, FR layer / protective layer / polarizing element / protective layer / retardation plate / adhesive layer, FR layer / protective layer / polarizing element / protective layer / PSA layer / retardation plate / FR layer / adhesive layer, FR layer / protective layer / polarizing element / protective layer / FR layer / PSA layer / retardation plate / adhesive layer, Protective layer / FR layer / polarizing element / protective layer / adhesive layer, FR layer / protective layer / polarizing element / protective layer / PSA layer / protective layer / protective layer / / FR layer and FR layer / protective layer / polarizing element
  • FR layer / protective layer / polarizing element / protective layer As a more preferable configuration of the polarizing plate, FR layer / protective layer / polarizing element / protective layer, FR layer / protective layer / polarizing element / protective layer / FR layer, FR layer / protective layer / polarizing element / protective layer / retardation plate / adhesive layer, FR layer / protective layer / polarizing element / protective layer / PSA layer / retardation plate / FR layer / adhesive layer, FR layer / protective layer / polarizing element / protective layer / FR layer / PSA layer / retardation plate / adhesive layer, FR layer / protective layer / polarizing element / protective layer / PSA layer / protective layer / protective layer / FR layer and FR layer / protective layer / polarizing element / protective layer / FR layer / PSA layer / FR layer / protective Layer / protective Layer / protective Layer
  • a particularly preferred configuration of the polarizing plate is FR layer / protective layer / polarizing element / protective layer / FR layer, FR layer / protective layer / polarizing element / protective layer / retardation plate / FR layer / adhesive layer, FR layer / protective layer / polarizing element / protective layer / FR layer / PSA layer / retarder / adhesive layer, and FR layer / protective layer / polarizing element / protective layer / FR layer / PSA layer / FR layer / protective layer / It is polarizing element / protective layer / FR layer, and flame retardance can be particularly improved in these configurations.
  • an antiglare layer hereinafter also referred to as “AG layer”
  • an antireflection layer hereinafter also referred to as “AR layer”
  • LR layer a low reflection layer
  • the AG layer contains, on the surface of the polarizing plate, a resin composition and an inorganic filler containing silica, aluminum, titanium, or the like, or an organic filler such as acrylic or polystyrene, and is applied to the film surface or the substrate surface. It is a layer for preventing glare by forming fine irregularities.
  • the AG layer is a layer formed from a mixture of a filler and a resin composition
  • the resin composition contains a halogen-free flame retardant, particularly a compound having a phosphaphenanthrene skeleton or a phosphazene skeleton. It can also exhibit strong flame retardancy.
  • the AR layer is made of a multilayer film of materials having different refractive indexes, specifically titanium oxide, zinc oxide, silica, magnesium oxide, aluminum oxide, etc., and a low refractive index layer and a high refractive index layer are laminated. This is a layer designed to prevent the reflected light generated in each surface field from interfering with each other and preventing reflection at the interface. The layer often consists of 2 to 4 layers.
  • the LR layer is formed by applying a low refractive index material (single layer) for the purpose of reducing only the reflection at the interface, thereby reducing the reflectance.
  • a low refractive index material single layer
  • the thickness of both the AR layer and the LR layer is generally 0.2 ⁇ m or less, and even if such a layer of 0.2 ⁇ m or less is on the surface of the polarizing plate, the flame retardancy is affected. Absent. Therefore, even if it has an AR layer and / or an LR layer, the flame retardancy of the polarizing plate can be realized.
  • the flame-retardant polarizing plate according to the present invention can satisfy the flammability test FMVSS 302 of American automobile interior materials, and therefore can satisfy the flame retardancy and flame spreadability of interiors required for automobiles.
  • FMVSS Federal Motor Vehicle Safety Standard
  • FMVSS Federal Motor Vehicle Safety Standard
  • a test piece having a size of 102 mm ⁇ 356 mm was allowed to stand for 24 hours at 21 ° C. and 50% RH, and then the flame height was 38 mm, and 15 seconds in a location 19 mm from the center of the end. Let the flame contact. It is required to extinguish the flame within a flame contact speed of 102 mm / min or less, or within a combustion distance of 51 mm and 60 seconds from the combustion time measurement line.
  • the polarizing plate according to the present invention has high durability and maintains transparency and adhesion even when exposed to a flame, high temperature, high humidity, or high intensity light for a long time. I can do it.
  • the high flame retardancy can satisfy the flammability test FMVSS 302 of American automobile interior materials. Utilizing such characteristics, the flame retardancy and flame spreadability are required. It is useful for the use of a durable and reliable liquid crystal display, and is particularly useful for the display of vehicles, various industrial instruments, household appliances, and the like.
  • Example 1 Production of protective layer (TAC) having FR layer 40 parts by mass of pentaerythritol hexaacrylate (manufactured by Nippon Kayaku Co., Ltd., KAYARAD PET-30), 2,2,4,4,6,6-hexakis 60 parts by mass of [2- (methacryloyloxy) ethoxy] -1,3,5,2,4,6-triazatriphospholine (Idemitsu Petrochemical Co., Ltd., PPZ monomer), IRGACURE 184 (Ciba Specialty Chemicals Co., Ltd.) ) Was mixed 5 parts by weight, 2-butanone 82 parts by weight, and cyclopentanone 18 parts by weight to prepare a resin composition.
  • TAC protective layer
  • Bar coater ROD # 6 (manufactured by Tester Sangyo Co., Ltd.) is applied to a triacetyl cellulose film (TAC) (manufactured by BRIGHT, P980GL) having a film thickness of 60 ⁇ m so that the film thickness after solvent drying is 5 ⁇ m.
  • TAC triacetyl cellulose film
  • the coating was applied and dried at 70 ° C. for 2 minutes.
  • the dried coating film was irradiated with ultraviolet rays using a high-pressure mercury lamp (integrated light amount 400 mJ / cm 2 ) in the air to produce an FR layer. Two sets of TACs having this FR layer were produced.
  • the obtained TAC having the FR layer was immersed in an aqueous solution adjusted to pH 11 with sodium hydroxide in an alkaline aqueous solution for 10 minutes, and the contact angle of water on the TAC film surface was changed from 80.0 ° to 52.3 °. Reduced.
  • the film obtained by the boric acid treatment was treated for 5 minutes in a 55 ° C. aqueous solution containing 3.0% by mass of boric acid while being stretched 5.0 times.
  • the film obtained by the boric acid treatment was washed with water at 30 ° C. for 15 seconds while maintaining the tension state.
  • the obtained film was immediately dried at 70 ° C. for 9 minutes to obtain a polarizing element having a thickness of 28 ⁇ m.
  • Example 2 A TAC having two sets of FR layers was produced in the same manner as in Example 1 (1). Two polarizing elements were produced in the same manner as (2) of Example 1 except that the dye adsorption time was changed from 3 minutes to 1 minute 30 seconds. The TAC surface of the TAC having the FR layer was bonded to one surface of the polarizing element, a single TAC was bonded to the other surface of the polarizing element, and two sets of FR layer / TAC / polarizing element / TAC were produced. .
  • an aqueous polyvinyl alcohol solution an aqueous solution of 4% by weight of polyvinyl alcohol (Nippon Vinegar Bipoval, NH-26) was used.
  • An adhesive layer having a thickness of 22 ⁇ m is provided between the two sets of FR layers / TAC / polarizing element / TAC TAC surfaces using an adhesive (PTR-3000 manufactured by Nippon Kayaku Co., Ltd.), and the TAC surfaces are Paste the following: A polarizing plate in which these elements were laminated in the order of FR layer / TAC / polarizing element / TAC / adhesive layer / TAC / polarizing element / TAC / FR layer was produced.
  • Example 3 A TAC having four sets of FR layers was produced in the same manner as in Example 1 (1).
  • Two polarizing elements were produced in the same manner as (2) of Example 1 except that the dye adsorption time was changed from 3 minutes to 1 minute 30 seconds.
  • Two sets of FR layer / TAC / polarizing element / TAC / FR layer were produced by bonding to the TAC surface of the TAC having two sets of FR layers and both surfaces of the polarizing element, respectively.
  • an aqueous polyvinyl alcohol solution an aqueous solution of 4% by weight of polyvinyl alcohol (Nippon Vinegar Bipoval, NH-26) was used.
  • An adhesive layer having a thickness of 22 ⁇ m is provided between the two layers of the FR layer / TAC / polarizing element / TAC / FR layer using an adhesive (PTR-3000 manufactured by Nippon Kayaku Co., Ltd.). Laminate the layer surfaces together, the following: A polarizing plate in which these elements were laminated in the order of FR layer / TAC / polarizing element / TAC / FR layer / adhesive layer / FR layer / TAC / polarizing element / TAC / FR layer was produced.
  • Example 4 In preparation of the TAC film having the FR layer of Example 2, as a resin composition, 50 parts by mass of pentaerythritol hexaacrylate (KAYARAD PET-30 manufactured by Nippon Kayaku Co., Ltd.), containing no halogen and having flame retardancy 50 parts by mass of 2,2,4,4,6,6-hexakis [2- (methacryloyloxy) ethoxy] -1,3,5,2,4,6-triazatriphospholine, IRGACURE 184 (Ciba Specialty) A polarizing plate was prepared in the same manner as in Example 2 except that a resin composition prepared by mixing 5 parts by mass of Chemicals), 82 parts by mass of 2-butanone and 18 parts by mass of cyclopentanone was used. did.
  • Example 5 In the preparation of the TAC film having the FR layer of Example 2, as a resin composition, 60 parts by mass of pentaerythritol hexaacrylate (KAYARAD PET-30 manufactured by Nippon Kayaku Co., Ltd.), containing no halogen and having flame retardancy 40 parts by mass of 2,2,4,4,6,6-hexakis [2- (methacryloyloxy) ethoxy] -1,3,5,2,4,6-triazatriphospholine, IRGACURE 184 (Ciba Specialty) A polarizing plate was prepared in the same manner as in Example 2 except that a resin composition prepared by mixing 5 parts by mass of Chemicals), 82 parts by mass of 2-butanone and 18 parts by mass of cyclopentanone was used. did.
  • Example 6 In the preparation of the TAC film having the FR layer of Example 2, as a resin composition, 80 parts by mass of 2,2,4,4,6 pentaerythritol hexaacrylate (KAYARAD PET-30 manufactured by Nippon Kayaku Co., Ltd.) was used.
  • KAYARAD PET-30 manufactured by Nippon Kayaku Co., Ltd.
  • a polarizing plate was produced in the same manner as in Example 2 except that a resin composition prepared by mixing 82 parts by mass of 2-butanone and 18 parts by mass of cyclopentanone was used.
  • Example 7 In the preparation of the TAC film having the FR layer of Example 2, 25 parts by mass of 2,2,4,4,6 as a resin composition pentaerythritol hexaacrylate (KAYARAD PET-30 manufactured by Nippon Kayaku Co., Ltd.) , 6-hexakis [2- (methacryloyloxy) ethoxy] -1,3,5,2,4,6-triazatriphosphorine, 75 parts by mass, IRGACURE 184 (manufactured by Ciba Specialty Chemicals), 5 parts by mass, A polarizing plate was produced in the same manner as in Example 2 except that a resin composition prepared by mixing 82 parts by mass of 2-butanone and 18 parts by mass of cyclopentanone was used.
  • KAYARAD PET-30 manufactured by Nippon Kayaku Co., Ltd.
  • IRGACURE 184 manufactured by Ciba Specialty Chemicals
  • Example 8 In preparation of a TAC film having an FR layer in Example 2, as a resin composition, 60 parts by mass of pentaerythritol hexaacrylate (KAYARAD PET-30 manufactured by Nippon Kayaku Co., Ltd.), 2, 2, 4, 4, 6, 40 parts by mass of 6-hexakis (phenoxy) -1,3,5,2,4,6-triazatriphospholine (manufactured by Otsuka Chemical Co., Ltd. SPS-100) and 5 IRGACURE 184 (manufactured by Ciba Specialty Chemicals) A polarizing plate was produced in the same manner except that a resin composition prepared by mixing 82 parts by mass of 2-partanone and 18 parts by mass of cyclopentanone was used.
  • Example 9 In preparation of a TAC film having an FR layer in Example 2, as a resin composition, 60 parts by mass of pentaerythritol hexaacrylate (KAYARAD PET-30 manufactured by Nippon Kayaku Co., Ltd.), a compound example PP-18 having flame retardancy 40 parts by mass (Nippon Kayaku FRM-1000), 5 parts by mass IRGACURE 184 (Ciba Specialty Chemicals), 82 parts by mass of 2-butanone and 18 parts by mass of cyclopentanone were mixed. A polarizing plate was produced in the same manner except that the resin composition prepared above was used.
  • Example 10 In preparing a TAC film having an FR layer in Example 2, 55 parts by mass of pentaerythritol hexaacrylate (KAYARAD PET-30, manufactured by Nippon Kayaku Co., Ltd.) as a resin composition, a compound example PP-18 having flame retardancy (Nippon Kayaku Co., Ltd. FRM-1000) 45 parts by mass, IRGACURE 184 (Ciba Specialty Chemicals) 5 parts by mass, 2-butanone 82 parts by mass, cyclopentanone 18 parts by mass A polarizing plate was produced in the same manner except that the resin composition prepared above was used.
  • KAYARAD PET-30 manufactured by Nippon Kayaku Co., Ltd.
  • FRM-1000 flame retardancy
  • IRGACURE 184 Ciba Specialty Chemicals
  • Example 11 In preparation of a TAC film having an FR layer in Example 2, as a resin composition, 70 parts by mass of pentaerythritol hexaacrylate (KAYARAD PET-30 manufactured by Nippon Kayaku Co., Ltd.), Compound Example PP-1 (manufactured by Sanko) Except that a resin composition prepared by mixing 35 parts by mass, IRGACURE 184 (manufactured by Ciba Specialty Chemicals), 5 parts by mass, 82 parts by mass of 2-butanone and 18 parts by mass of cyclopentanone was used. A polarizing plate was produced in the same manner.
  • Example 12 In the production of the TAC film having the FR layer in Example 1, a polarizing plate was produced in the same manner as in Example 1 except that the film thickness of the FR layer after solvent drying was changed to 2 ⁇ m instead of 5 ⁇ m.
  • Example 13 83 parts by mass of n-butyl acrylate, 1 part by mass of 2-hydroxyethyl acrylate, and 12 parts by mass of N, N-dimethylacrylamide are dissolved in 185 parts by mass of ethyl acetate, and 0.05 part by mass of azobisisobutyronitrile was added and reacted at 70 ° C. for 5 hours to obtain an acrylic copolymer resin (weight average molecular weight: 1,3500,000, Tg: ⁇ 37 ° C.).
  • an acrylic copolymer resin solution (viscosity: 2,000 cps / 25 ° C.) prepared with ethyl acetate so that the resin content is 20% by mass, with respect to 100 parts by mass of the resin solid content of the acrylic copolymer resin solution, Tolylene diisocyanate (3 mole) adduct of 0.5 parts by weight of trimethylolpropane (1 mole), 0.5 part by weight of ⁇ -glycidoxypropylmethoxysilane, and 9,10-dihydro-9-oxa-10- 30 parts by mass of phosphaphenanthrene-10-oxide (manufactured by Sanko Co., Ltd.) was mixed and stirred to obtain an adhesive resin composition.
  • TAC / polarizing element / TAC Two sets of TAC / polarizing element / TAC obtained by bonding using a 4% by weight aqueous solution of polyvinyl alcohol so that the polarizing element obtained according to Example 1 (2) is sandwiched between two TACs are prepared.
  • a pair of TAC / polarizing element / TAC was bonded by providing an adhesive layer having a thickness of 22 ⁇ m between them using an adhesive resin composition.
  • an adhesive layer having a thickness of 22 ⁇ m formed on the release film using the adhesive resin composition was pasted on one TAC surface of the obtained laminate, and the following: TAC / polarizing element / TAC / adhesive layer containing phosphaphenanthrene compound / TAC / polarizing element / TAC / adhesive layer containing phosphaphenanthrene compound / release film Produced.
  • Example 14 Instead of 30 parts by mass of 9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide (HCA manufactured by Sanko Co., Ltd.), 20 parts by mass of cyclic phenoxyphosphazene (SPE-100 manufactured by Otsuka Chemical Co., Ltd.) A polarizing plate was produced in the same manner as in Example 13 except for the points used.
  • Example 15 Instead of 30 parts by mass of 9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide (manufactured by Sanko Co., Ltd., HCA), 40 parts by mass of cyclic phenoxyphosphazene (SPE-100, manufactured by Otsuka Chemical Co., Ltd.) A polarizing plate was produced in the same manner as in Example 13 except for the points used.
  • Example 16 80 parts by mass of n-butyl acrylate, 1 part by mass of 2-hydroxyethyl acrylate, 12 parts by mass of N, N-dimethylacrylamide, hexa (methacryloxyethylenedioxy) cyclotriphosphazene (PPZ monomer manufactured by Idemitsu Petrochemical Co., Ltd.) 8 A mass part is dissolved in 185 parts by mass of ethyl acetate, 0.05 part by mass of azobisisobutyronitrile is added, and the mixture is reacted at 70 ° C. for 5 hours to obtain an acrylic copolymer resin (weight average molecular weight: 1,3500, 000, Tg: ⁇ 37 ° C.).
  • an acrylic copolymer resin solution (viscosity 2,000 cps / 25 ° C.) prepared with ethyl acetate so that the resin content becomes 20% by mass was added to 100 parts by mass of the resin solid content of the acrylic copolymer resin solution.
  • 0.5 parts by mass of ⁇ -glycidoxypropylmethoxysilane, and 9,10-dihydro-9-oxa-10-phospho 30 parts by mass of phenanthrene-10-oxide (manufactured by Sanko Co., Ltd.) was mixed and stirred to obtain a pressure-sensitive adhesive resin composition.
  • TAC / polarizing element / TAC Two sets of TAC / polarizing element / TAC obtained by bonding using a 4% by weight aqueous solution of polyvinyl alcohol so that the polarizing element obtained according to Example 1 (2) is sandwiched between two TACs are prepared.
  • a pair of TAC / polarizing element / TAC was bonded by providing an adhesive layer having a thickness of 22 ⁇ m between them using an adhesive resin composition.
  • an adhesive layer having a thickness of 22 ⁇ m formed on the release film using the adhesive resin composition was pasted on one TAC surface of the obtained laminate, and the following: A polarizing plate in which these elements were laminated in the order of TAC / polarizing element / TAC / adhesive layer containing a TAC / phosphazene compound / TAC / polarizing element / TAC / adhesive layer containing a phosphazene compound / release film was prepared.
  • Example 17 In production of a TAC film having an FR layer in Example 2, 2,2,4,4,6,6-hexakis [2- (methacryloyloxy) ethoxy] -1,3 having flame retardancy was used as a resin composition.
  • Example 4 In the same manner as in Example 1 except that a TAC film having no FR layer was used instead of the TAC film having an FR layer, the following: TAC / Polarizing element / TAC A polarizing plate in which these elements were laminated in this order was prepared.
  • the flame retardant layer according to the present invention does not decrease the transmittance and the degree of polarization of the polarizing element, and has high flame resistance. It is shown that a polarizing plate satisfying FMVSS 302, which is a US safety standard, is obtained.
  • FMVSS 302 which is a US safety standard.

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Abstract

L'invention concerne une plaque de polarisation ignifuge qui contient un polariseur et une couche ignifuge d'épaisseur comprise entre 0,1 et 100μｍ. Laquelle couche ignifuge contient : un produit durci d'une composition de résine qui contient 5 à 80% en masse d'un agent ignifuge exempt d'halogène qui possède au moins un groupe (méth)acryloyl, ou d'un agent ignifuge exempt d'halogène ne possédant pas de groupe (méth)acryloyl, et un composé (méth)acrylate exempt d'halogène et ne présentant pas de propriétés ignifuges ; ou un produit durci d'une composition de résine qui contient 10 à 99,9% en masse d'un agent ignifuge exempt d'halogène qui possède au moins un groupe (méth)acryloyl.
PCT/JP2017/019690 2016-05-27 2017-05-26 Plaque de polarisation ignifuge, et dispositif d'affichage à cristaux liquides mettant en œuvre celle-ci WO2017204327A1 (fr)

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TW201811843A (zh) 2018-04-01
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JPWO2017204327A1 (ja) 2019-03-22
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