TW201811843A - Flame-retarding polarizer and liquid crystal display device using the polarizer - Google Patents

Abstract

Provided is a flame-retarding polarizer comprises a flame-retarding layer having thickness of 0.1~100 [mu]m, and a polarizer element, wherein the flame-retarding layer comprises 5~99 mass% of a compound having phenanthrene skeleton and/ or a compound having phosphazene skeleton.

Description

 Flame retardant polarizing plate and liquid crystal display device using the same  

The present invention relates to a flame retardant polarizing plate and a liquid crystal display device using the polarizing plate.

In recent years, due to the spread of liquid crystal displays, optical films have been industrially produced and used in large quantities. The liquid crystal display body starting from a small object display such as a watch or an electronic desktop computer is gradually used in a personal computer, a liquid crystal television, a liquid crystal projector, a vehicle-mounted instrument panel, a vehicle-mounted central control panel, and a vehicle. A navigation system, a head-up display, or the like is used as an in-vehicle monitor.

In the past, the premise of the display was gradually developed in the general household as a home appliance capable of high-quality viewing, so high brightness was required. High contrast, but in recent years, the trend is gradually demanding safety, especially flame retardancy, in a more stringent use environment. In terms of flame retardancy, it is mainly required to have three properties of "non-burning performance", "non-combustion performance", and "performance even if burned out" due to flame or heat. In particular, it is assumed that a vehicle-mounted module has a fire in the vehicle, and in order to suppress the burning and the generation of toxic gas, the vehicle-mounted module is strongly required to have "non-combustion performance" and/or "performance even if the combustion is extinguished".

In the past, the vehicle-mounted module was provided with a polycarbonate plate, an acrylic plate, a heat dissipation frame (Louver jig) or the like as a front panel of the display to protect the display. On the other hand, in recent years, from the viewpoint of imparting pattern design and touch panel functions and securing the space inside the vehicle, such a front panel or the like is gradually removed to make the display stand on the interior decorative surface of the vehicle. . Therefore, the flame retardancy required for the display is further improved.

When the polarizing plate of the constituent elements of the liquid crystal display panel is burned, the display function of the liquid crystal monitor disappears and safety information or the like cannot be displayed, so that the risk is improved. Therefore, the polarizing plate attached to the outermost surface of the display is also strongly required to have "non-combustion performance" and/or "performance even if it is burned out". At the same time, from the point of view of the application of insurance for home wealth, there is also a case where the cost of insurance is low when using a non-flammable home appliance, and in recent years, home appliances are also required to be flame retardant. As such, home appliances and in-vehicle displays are required to be flame retardant and polarizers are also required to be flame retardant.

In general, a polarizing plate can be laminated on both sides of a polarizing element obtained by adsorbing a polyvinyl alcohol (hereinafter also referred to as "PVA") film as an iodine or a dichroic dye of a dichroic dye and performing elongation processing. Next, a cellulose triacetate (hereinafter also referred to as "TAC") film is further produced by providing a pressure-sensitive adhesive layer (hereinafter also referred to as "PSA") on the surface of the TAC film. Since PVA, TAC, and PSA are equivalent to ordinary plastic and cellulose films, they do not have the "non-combustion performance" required for the vehicle-mounted module, and the "performance even if the combustion is extinguished". Extinguishing. Therefore, a technique for making a polarizing plate into flame retardant is required.

When it is called "non-combustion performance" and/or "performance even if it is extinguished by burning", it is usually made to contain a flame retardant. For example, it is known that TAC usually contains triphenyl phosphate (hereinafter also referred to as "TPP") as a plasticizer. Patent Document 1 describes that it is possible to impart flame retardancy by containing such a phosphorus-based compound, and it is known to be applied to a polarizing plate.

Further, as a technique for imparting flame retardancy to a polarizing plate, Patent Document 2 describes a technique in which a flame retardant woven fabric is a geometric pattern. Further, Patent Document 3 describes a technique in which at least 10% by mass of a halogen-free flame retardant such as a phosphate ester is contained in the pressure-sensitive adhesive.

 [Previous Technical Literature]    [Patent Literature]  

[Patent Document 1] Japanese Patent Laid-Open Publication No. 2004-352807

[Patent Document 2] Japanese Patent Laid-Open No. 6-130223

[Patent Document 3] Japanese Patent Laid-Open Publication No. 2014-515049

However, even if a phosphorus-based compound such as TPP is contained in Patent Document 1, the in-vehicle monitor and the home appliance are not required to have sufficient flame retardancy. When the content of the phosphorus-based compound such as TPP is increased to improve the flame retardancy, there is a problem that the transparency is lowered or the TPP is precipitated in the durability test. There are also reports that TPP will promote TAC corrosion. In recent years, since TPP promotes decomposition of TAC in a high-temperature and high-humidity environment, TAC which does not contain TPP is spreading. This is the main reason why the flame retardancy of the polarizing plate is further lowered.

When the phosphate is contained in the adhesive as described in Patent Document 3, it is affected by phosphoric acid, and it is acidic in the polarizing plate system and causes a problem that TAC accelerates decomposition. Or, depending on the concentration of the phosphate, the adhesion of the adhesive or the adhesive is lowered and peeling and foaming occur in the display. Further, there is a problem that white turbidity and a low transmittance of the film are lowered due to precipitation of the phosphate. Therefore, the technique of Patent Document 3 is used to improve the flame retardancy of the polarizing plate, and is not suitable on a practical surface.

Moreover, the number of film sheets constituting the polarizing plate is increased year by year. For example, a polarizing plate having a phase difference plate having broadband decolorizing property is known to have a one-quarter wave plate and a one-half wave plate for making the laminated adhesive layer necessary. Further, it is necessary to satisfy the number of films necessary for the prevention of surface scratches, the anti-reflection hard coat layer (HC layer), the antireflection layer, or the antiglare layer. The number of laminated films is also large, which is also a cause of further increasing the flammability of the polarizing plate. In the case where the number of layers is substantially increased in flammability, it is further required to impart flame retardancy.

Accordingly, it is an object of the present invention to provide a flame retardant polarizing plate capable of achieving high flame retardancy, particularly "non-combustion performance" and/or "performance even if combustion is extinguished" and liquid crystal using the same. Display device.

It is preferable that the present invention has at least one of high transparency, high degree of polarization, high temperature or high temperature and high humidity durability (long-term exposure under high temperature or high temperature and high humidity conditions, and less deterioration).

In order to solve the above problems, the inventors of the present invention have intensively studied and found a polarizing plate characterized in that a layer having a specific thickness is provided on the surface layer side of the polarizing element, and the layer contains: a predetermined amount of one or more (A) a halogen-free flame retardant based on an acrylonitrile group or a halogen-free flame retardant having no (meth)acryl fluorenyl group, and a (meth) acrylate compound which does not contain a halogen and which does not exhibit flame retardancy a cured product of the resin composition; or a cured product of a resin composition containing a predetermined amount of a halogen-free flame retardant having one or more (meth) acrylonitrile groups; the polarizing plate can achieve transparency High in nature and high in polarization, even at high temperatures. The present invention has been completed by exposure to high temperature and high humidity for a long period of time, deterioration of the flame retardant performance, "non-combustion performance" and "performance even if the combustion is extinguished".

Further, the present inventors have found that a polarizing plate having a layer containing 5 to 99% by mass of a compound having a phosphaphenanthrene skeleton and/or a compound having a phosphazene skeleton can achieve transparency. High and high polarization, even at high temperatures. The present invention has been completed by exposing a polarizing plate which is exposed to a high temperature and high humidity for a long period of time, has little deterioration, and has high flame retardancy, particularly "non-combustion performance" and "performance even if it is extinguished by burning".

That is, the present invention relates to the following [X1] to [X10].

[X1]

A flame retardant polarizing plate comprising a flame retardant layer having a thickness of 0.1 to 100 μm and a polarizing element, wherein the flame retardant layer contains: 5 to 80% by mass of one or more (meth) propylene A halogen-free flame retardant or a halogen-free flame retardant having no (meth)acryl fluorenyl group, and a resin composition of a (meth) acrylate compound which does not contain a halogen and does not exhibit flame retardancy A cured product of a resin composition containing 10 to 99.9% by mass of a halogen-free flame retardant having one or more (meth) acrylonitrile groups.

[X2]

The flame-retardant polarizing plate according to [X1], wherein the halogen-free flame retardant having one or more (meth)acryl fluorenyl groups and the halogen-free (meth)acryl fluorenyl group are not contained. The flame retardant is a compound having a 10-sided oxy 9-oxa-10-phosphaphenanthrene skeleton or a phosphazene skeleton.

[X3]

The flame-retardant polarizing plate according to [X2], wherein the compound having a 10-sided oxy 9-oxa-10-phosphaphenanthrene skeleton is a compound represented by the formula (1): (wherein R ₁ is a (meth)acryloyl group or a substituent having a (meth)acryl fluorenyl group).

[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-triazatriphosphorane skeleton.

[X5]

A flame-retardant polarizing plate according to [X4], wherein the compound having the above-mentioned 1,3,5,2,4,6-triazatriphosphorane skeleton is a compound represented by the formula (2): (wherein R ₂ to R ₇ each independently represent a (meth)acryloyl group or a substituent having a (meth)acryl fluorenyl group).

[X6]

The flame retardant polarizing plate according to any one of the aspects of the present invention, wherein the halogen-free flame retardant having one or more (meth)acryl fluorenyl groups has two or more The (meth) acrylonitrile group, wherein the mass ratio of the halogen-free flame retardant having two or more (meth) acrylonitrile groups to the (meth) acrylate compound in the resin composition is 10: 88 to 75:23.

[X7]

The flame-retardant polarizing plate according to any one of the aspects of the present invention, wherein all or a part of the (meth) acrylate compound has a hydroxyl group and contains 25 to 90 masses in the resin composition. %.

[X8]

The flame-retardant polarizing plate according to any one of [1], wherein the flame-retardant layer is selected from the group consisting of an adhesive layer, an adhesive layer, a hard coat layer, and a protective layer. .

[X9]

The flame-retardant polarizing plate according to any one of the aspects of the present invention, wherein the flame-retardant layer is provided on an environmentally exposed surface side and/or a light-exposed surface side of the polarizing element.

[X10]

A liquid crystal display device comprising the flame retardant polarizing plate according to any one of [X1] to [X9].

Moreover, the present invention relates to the following [Y1] to [Y10].

[Y1]

A flame retardant polarizing plate comprising a flame retardant layer having a thickness of 0.1 to 100 μm and a polarizing element, wherein the flame retardant layer contains 5 to 99% by mass of a compound having a phosphaphenanthrene skeleton and/or having phosphorus A compound of a nitrile skeleton.

[Y2]

The flame-retardant polarizing plate according to [Y1], wherein the flame-retardant layer contains: 5 to 80% by mass of a compound having a phosphaphenanthrene skeleton and/or a phosphazene skeleton, and a phosphorus compound as described above The compound of the phenanthrene skeleton and the compound having the phosphazene skeleton described above are cured products of a resin composition of a different (meth) acrylate compound; or 10 to 99.9% by mass of a (meth) acrylonitrile group having a phosphorus A cured product of a compound of a phenanthrene skeleton and/or a resin composition of a compound having a phosphazene skeleton having a (meth) acrylonitrile group.

[Y3]

The flame retardant polarizing plate according to [Y1] or [Y2], wherein the compound having a phosphophenanthrene skeleton is a compound having a 10-sided oxy-9-oxa-10-phosphaphenanthroline skeleton.

[Y4]

A flame-retardant polarizing plate according to [Y3], wherein the aforementioned compound having a 10-sided oxy-9-oxa-10-phosphaphenanthroline skeleton is a formula (1): (wherein R ₁ is a compound represented by a (meth)acryloyl group or a substituent having a (meth)acryl fluorenyl group).

[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-triazatriphosphorane skeleton.

[Y6]

The flame retardant polarizing plate according to [Y5], wherein the compound having the 1,3,5,2,4,6-triazatriphosphorane skeleton is: (wherein R ₂ to R ₇ are each independently a compound represented by a (meth)acryl fluorenyl group or a substituent thereof).

[Y7]

The flame retardant polarizing plate according to any one of the aspects of the present invention, wherein all or a part of the (meth) acrylate compound has a hydroxyl group and contains 25 to 90 masses in the resin composition. %.

[Y8]

The flame-retardant polarizing plate according to any one of [1], wherein the flame-retardant layer is selected from the group consisting of an adhesive layer, an adhesive layer, a hard coat layer, and a protective layer. .

[Y9]

The flame-retardant polarizing plate according to any one of [1], wherein the flame-retardant layer is provided on an environmentally exposed surface side and/or a light-exposed surface side of the polarizing element.

[Y10]

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 the liquid crystal display device using the same have high flame retardancy, and can realize "non-combustible performance" (non-combustible property) and/or "even burning flames". Disappearing performance" (difficult to burn).

Preferably, the present invention has at least one of "high transparency", "high degree of polarization", and "high temperature or high temperature and high humidity durability".

<flammable layer>

In a certain aspect, the flame retardant layer of the present invention (hereinafter also referred to as "FR layer" (Flame Resistance Layer)" is characterized in that it is a flame retardant layer (A) or flame retardant. Layer (B), the flame retardant layer (A) contains a predetermined amount of a halogen-free flame retardant having one or more (meth)acryl fluorenyl groups or no (meth) acrylonitrile group a halogen-containing flame retardant and a cured product of a resin composition of a (meth) acrylate compound which does not contain a halogen and which does not exhibit flame retardancy; and the flame retardant layer (B) contains a predetermined amount and has one A cured product of a resin composition of the above (meth)acrylonitrile-based halogen-free flame retardant.

In a certain aspect, the flame retardant layer of the present invention is characterized by comprising a flame retardant layer (C) having a compound having a phosphaphenanthrene skeleton and/or a compound having a phosphazene skeleton.

The flame retardant polarizing plate of the present invention is characterized by comprising a flame retardant polarizing plate selected from at least one of the flame retardant layers (A), (B), and (C) and a polarizing element.

Hereinafter, the term "flammability" means that the flame does not burn at a certain speed or higher (it is not easy to burn), or the fire after the fire is extinguished, or does not expand to a certain extent or more, for example, to satisfy the automobile interior material of the United States. Flammability test FMVSS 302. "Flame retardant" is a compound used to impart flame retardancy.

[flame retardant layer (A)]

The flame-retardant layer (A) contains (a) a predetermined amount of a halogen-free flame retardant having one or more (meth)acryl fluorenyl groups or a halogen-free one having no (meth) acrylonitrile group. A flame retardant agent and (b) a flame retardant layer of a cured product of a resin composition of a (meth) acrylate compound which does not contain a halogen and which does not exhibit flame retardancy.

(a) halogen-free flame retardant

The halogen-free flame retardant is a halogen-free flame retardant having one or more (meth)acryl fluorenyl groups or a halogen-free flame retardant having no (meth) acrylonitrile group. In the present specification, the (meth)acrylonitrile group means an acryloyl group or a methacryl group. "Halogen-free" means a compound which does not contain a halogen atom, for example, a fluorine, chlorine, bromine, or iodine atom. The content of the halogen-free flame retardant in the resin composition is 5 to 80% by mass, preferably 15 to 75% by mass, preferably 25 to 70% by mass, particularly preferably 35 to 65% by mass.

The halogen-free flame retardant is preferably a compound having a phosphophenanthrene skeleton or a phosphazene skeleton. By using these halogen-free flame retardants, the performance of flame retardancy can be remarkably improved. Further, when the phosphazene skeleton is a cyclic triphosphazene skeleton, it is more preferable because it can particularly enhance the flame retardancy function. The compound having a phosphaphenanthrene skeleton, a compound having a phosphazene skeleton, and a compound having a cyclotriphosphazene skeleton may be used singly or in combination of two or more kinds in any ratio.

<phosphorus phenanthrene compound>

The flame retardant having a phosphaphenanthrene skeleton is preferably a compound having a 10-sided oxy-9-oxa-10-phosphaphenanthroline skeleton. A compound having a 10-sided oxo-9-oxa-10-phosphaphenanthroline skeleton is represented by the formula (1): The compound represented is preferred.

In the formula (1), R ₁ is preferably selected from the group consisting of hydrogen, and an unsubstituted or substituted C 1 to 4 alkyl group or a C 1 to 4 alkoxy group, unsubstituted or substituted. a phenyl group, an unsubstituted or substituted naphthyl group, an unsubstituted or substituted phenoxy group, a substituted guanamine group, an alkyl group having an aryl group having 1 to 4 carbon atoms or a carbon number of 1 to 4 The group consisting of an alkoxy group, an alkyl ether group having an alkyl group having 1 to 4 carbon atoms having a substituent, a (meth) acryl fluorenyl group, and a substituent having a (meth) acryl fluorenyl group.

The substituent for the alkyl group having 1 to 4 carbon atoms and the alkoxy group having 1 to 4 carbon atoms is, for example, selected from the group consisting of a hydroxyl group, a carboxyl group, a cyano group and a glycidyl group. The substituent for the phenyl group is, for example, selected from the group consisting of a cyano group, a glycidyl group, a hydroxyl group, and a lower alkyl group having a hydroxyl group. The substituent for naphthyl is, for example, selected from the group consisting of 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)acrylylene group. . The substituent for the phenoxy group is, for example, selected from the group consisting of a hydroxyl group, a lower alkyl group having a glycidyl group, a (meth) acryl group, and a cyano group. The substituent for the guanamine group is, for example, selected from the group consisting of a hydroxyl group, a glycidyl group, and an iso-trisocyanate group. The "lower" system may be, for example, a linear or branched chain having 1 to 4 carbon atoms. Substituent groups are not limited by these.

The substituent having an acrylonitrile group is preferably the following formula: (n is an integer represented by 1 to 4, and m is a substituent represented by 0 or 1). The substituent having a methacryl fluorenyl group is preferably the following formula: (n is an integer represented by 1 to 4, and m is a substituent represented by 0 or 1). When R ₁ is a (meth) acrylonitrile group or a substituent having a (meth) acryl fluorenyl group, the performance of imparting flame retardancy is strongly exhibited, and it is possible to achieve high flame retardancy and maintain polarization with polarization. A polarizing plate having optical properties such as a transmittance equal to that of the element alone. Specifically, the polarizing plate provided with the flame-retardant layer can achieve good optical performance without causing deterioration in optical properties such as transmittance and polarization, even when compared with the polarizing plate before the flame-retardant layer is provided. Excellent flame retardancy.

Specific examples (PP-1 to PP-18) of the compound having a 10-sided oxy-9-oxa-10-phosphaphenanthrene skeleton represented by the formula (1) are shown below.

(M system means Cu, Ag, or Sb)

(n is an integer from 1 to 4)

<phosphazene compound>

The compound having a phosphazene skeleton is preferably a compound having a cyclic triphosphazene skeleton, and is preferably a compound having a 1,3,5,2,4,6-triazatriphosphorane skeleton. a compound having a 1,3,5,2,4,6-triazatriphosphorane skeleton, which is represented by the formula (2): The compound indicated is preferred.

In the formula (2), R ₂ to R ₇ are each independently selected, for example, from a hydrogen group, an alkoxy group having 1 to 4 carbon atoms, an unsubstituted or substituted phenyl group, an unsubstituted or substituted phenoxy group. A group consisting of a (meth) acrylonitrile group and a substituent having a (meth) acryl fluorenyl group. The substituent for the phenyl group is, for example, selected from the group consisting of a cyano group, a glycidyl group, a hydroxyl group, and an alkyl group having a hydroxyl group. The substituent for the phenoxy group is, for example, selected from the group consisting of a hydroxyl group, a lower alkyl group having a glycidyl group, a (meth) acryl group, and a cyano group, but is not limited thereto. R ₂ to R ₇ may be the same or different. It is particularly suitable that the R ₂ to R ₇ groups are each independently selected from the group consisting of the following substituents S-1 to the substituents S-4. Further, in the case of a substituent having a (meth)acrylinyl group, the substitution position of the (meth)acrylinyl group is preferably at the terminal end, but may be substituted as a side chain of the main chain in the substituent.

(n is an integer from 1 to 4, and m is 0 or 1)

(n represents an integer from 1 to 4, and m represents 0 or 1).

R ₂ to R ₇ are each independently a (meth) acryl fluorenyl group or a substituent having a (meth) acryl fluorenyl group, for example, when the substituent group S-3 or the substituent group S-4 is used, flame retardancy can be obtained. A flame-retardant layer having improved properties and hardness, and a polarizing plate having the flame-retardant layer has high flame retardancy and can achieve optical properties such as transmittance equivalent to that of a non-flammable layer. R ₂ to R ₇ may all be a (meth) acrylonitrile group or a substituent having a (meth) acryl fluorenyl group, or 1 to 5 of R ₂ to R ₇ may be a (meth) acryl fluorenyl group or A substituent having a (meth) acrylonitrile group. The polarizing plate provided with the flame-retardant layer can achieve better optical performance and excellent flame retardancy than when a compound having a 10-sided oxy-9-oxa-10-phosphaphenanthrene skeleton is used. Sex.

(b) (meth) acrylate compound which does not contain halogen and does not exhibit flame retardancy

In some aspects, the (meth) acrylate compound does not contain a halogen and does not exhibit flame retardancy. As the (meth) acrylate compound, a conventional (meth) acrylate monomer compound such as a photopolymerization type or a thermosetting type can be used. For example, the (meth) acrylate monomer compound (meth) is disclosed in the "ultraviolet curing system" (published by the General Technology Center, Kato Kasei, p. 259-303). A compound of an acrylonitrile group, but is not limited by the above. The (meth) acrylate compound which does not contain a halogen and does not exhibit flame retardancy may have one or more (meth) acrylonitrile groups, and preferably has 2 to 6. When the resin composition contains a (meth) acrylate compound having two or more (meth) acrylonitrile groups, the physical strength of the flame-retardant layer can be further improved, and the hardness and the adhesion can be further improved. The durability of the polarizing plate is more fully maintained.

Examples of the compound having a (meth) acrylate group which does not contain a halogen and which does not exhibit flame retardancy include a (meth)acrylic acid alkyl ester or a poly(meth)acrylic acid acrylate having a carbon number of 1 to 4, preferably (meth) acrylate having a neopentyl alcohol skeleton, a neopentyl glycol skeleton, a trimethylolpropane skeleton, a bisphenol A skeleton, a bisphenol F skeleton, a dicyclopentadiene skeleton, and an iso-cyanuric acid ring The compound is particularly preferably a (meth) acrylate compound having a neopentyl alcohol skeleton, a neopentyl glycol skeleton, a trimethylolpropane skeleton, or an iso-cyanocyanate ring. The (meth) acrylate compound can be used alone or in combination of two or more.

The total content of the (meth) acrylate compound which does not contain a halogen and which does not exhibit flame retardancy in the resin composition is preferably from 20 to 95% by mass, preferably from 25 to 95% by mass. In order to have sufficient physical strength by the flame retardant layer, it is preferred to contain 30 to 95% by mass of a (meth) acrylate compound having two or more (meth) acrylonitrile groups in the resin composition. It is preferably 40 to 95% by mass, more preferably 50 to 95% by mass. Further, in order to obtain a flame retardant layer capable of improving the durability of the polarizing plate, it is preferable to contain 50 to 95% by mass of the resin composition having 3 or more (meth) acrylonitrile groups. The (meth) acrylate compound is preferably 60 to 95% by mass, more preferably 70 to 95% by mass. By using a resin composition containing 30% by mass or more of a (meth) acrylate compound having two or more acrylonitrile groups, since it is a layer generally called a hard coat layer, it is possible to obtain JIS in Japanese industrial specifications. A layer having a surface hardness of H or more as defined in K 5600-5-4 is preferred. The surface hardness of the flame retardant layer is preferably 2H or more, and particularly preferably 3H or more.

Further, the (meth) acrylate compound which does not contain a halogen and does not exhibit flame retardancy is preferably a (meth) acrylate compound having a hydroxyl group in the molecule. By mixing a (meth) acrylate compound having a hydroxyl group in the resin composition, the adhesion between the flame-retardant layer and the polarizing element can be further improved. In particular, when a cellulose-based film, particularly cellulose triacetate (TAC) and other transparent cellulose acetate-based films are used as the protective layer of the polarizing element, the adhesion between the protective layer and the flame-retardant layer of the polarizing element can be improved. Sex is especially good. The content of the (meth) acrylate compound having a hydroxyl group is, for example, 25 to 90% by mass in the resin composition, preferably 30 to 80% by mass, preferably 40 to 70% by mass, more preferably 45 to 5%. 65% by mass.

Examples of the (meth) acrylate compound having a hydroxyl group in the molecule include a reaction product of trimethylolpropane triepoxypropyl ether and acrylic acid [DENACOL DA-321 瀬 瀬 ( 、 、 ), Glycerol diacrylate [EPOXYESTER 80MFA Kyoeisha Oil Co., Ltd.], propylene glycol diepoxypropyl ether and acrylic acid reaction product [DENACOL DA-911 Changyi Industry Co., Ltd.], phthalic acid diepoxy Reaction product of propyl ether and acrylic acid [DENACOL DA-721 manufactured by Nippon Oil Co., Ltd.], neopentyl alcohol triacrylate [KAYARAD PET-30 Nippon Chemical Co., Ltd.], 1,6-hexanediol Reaction product of diepoxypropyl ether and acrylic acid [KAYARAD R-167 Nippon Kayaku Co., Ltd.], reaction product of glycerol triepoxypropyl ether and acrylic acid [DENACOL DA-314 Changchun Industry Co., Ltd. ], glycerol dimethacrylate [made by BLEMMER GMR Nippon Oil & Fats Co., Ltd.], glycerin acrylate methacrylate [made by BLEMMER GAM Nippon Oil & Fats Co., Ltd.], ethylene glycol diepoxypropyl ether and (methyl) Acetic acid reaction product [DENACOL DM-811 Changchun Industry Co., Ltd.], diethylene glycol diepoxypropyl ether and (meth)acrylic acid Reaction product [DENACOL DM-851, manufactured by Nagase Industry Co., Ltd.], reaction product of bisphenol A diglycidyl ether and acrylic acid [KAYARAD R-115 Nippon Chemical Co., Ltd.], stearic acid modification Pentaerythritol diacrylate [ARONIX M-233 East Asia Synthetic Co., Ltd.], polyethylene glycol/polybutylene glycol methacrylate [BLEMMER PET series made from Japanese fats and oils], polypropylene glycol methacrylate Ester [BLEMMER PP-330, PP-500, PP-800 Japanese fats and oils], polyethylene glycol methacrylate [BLEMMER PE-90, PE-200, PE-350 Japanese fat (stock) system] , phenoxy hydroxypropyl acrylate [ARONIX M-5700 East Asia Synthetic Co., Ltd.], 2-hydroxypropyl methacrylate [GE-650 Mitsubishi Gas (stock)], 2-hydroxypropyl acrylate [HPA Osaka] Organic (manufactured by the company), 2-hydroxyethyl methacrylate [GE-610 Mitsubishi Gas Co., Ltd.], 2-hydroxyethyl acrylate [HEA Osaka Organic Co., Ltd.], glycerol methacrylate [BLEMMER] GLM Nippon Oil & Fats Co., Ltd., reaction product of butyl epoxidized propyl ether and acrylic acid [DENACOL DA-151 瀬 瀬 ( 、 、], butanediol monoacrylate [SR-676 SATOMER (share) system ]Wait. Preferred are neopentyl alcohol triacrylate, a reaction product of 1,6-hexanediol diepoxypropyl ether and acrylic acid, 2-hydroxyethyl methacrylate, 2-hydroxyethyl acrylate, and double The reaction product of phenol A diglycidyl ether and acrylic acid, etc., but is not limited thereto. As a (meth) acrylate compound having a hydroxyl group in the molecule, neopentyl alcohol triacrylate (KAYARAD PET-30 manufactured by Nippon Kayaku Co., Ltd.) is most preferable because it can maximize the wet heat durability of the polarizing plate.

A halogen-free flame retardant having a (meth) acrylonitrile group or a halogen-free flame retardant having no (meth) acrylonitrile group, and a (meth) group which does not contain a halogen and does not exhibit flame retardancy The proportion of the acrylate compound is preferably from 5:95 to 80:20. When the blending ratio is in this range, it has a flame retardancy and an effect of achieving high transparency and smooth film forming properties. In particular, when the halogen-free flame retardant having a (meth) acrylonitrile group has two or more (meth) acrylonitrile groups, the above ratio is from 10:88 to 75:23 by mass ratio because High flame retardancy, high hardness, adhesion, and high durability are preferred. In particular, from 25:73 to 68:30, since flame retardancy and transparency are particularly high and durability is improved, it is preferable.

(c) other ingredients

The resin composition can further contain a polymerization initiator. The polymerization initiator is selected according to the type of the polymerizable monomer such as the halogen-free flame retardant having a (meth) acrylonitrile group and the (meth) acrylate compound which does not contain a halogen and which does not exhibit flame retardancy. When the polymerizable monomer is an ultraviolet curing type, it is preferably an ultraviolet polymerization initiator. The ultraviolet polymerization initiator is, for example, 2-methyl-1-[4-(methylthio)phenyl]-2-N-morpholinylpropane-1 (IRGACURE 907 manufactured by CIBA SPECIALTY CHEMICALS), 1 -Hydroxycyclohexyl phenyl ketone (IRGACURE 184 manufactured by CIBA SPECIALTY CHEMICALS), 4-(2-hydroxyethoxy)-phenyl(2-hydroxy-2-propyl) ketone (IRGACURE 2959, manufactured by CIBA SPECIALTY CHEMICALS), 1 -(4-dodecylphenyl)-2-hydroxy-2-methylpropan-1-one (Darocur 953 by Merck), 1-(4-isopropylphenyl)-2-hydroxy-2-methyl Propane-1-one (Darocur 1116 manufactured by Merck), 2-hydroxy-2-methyl-1-phenylpropan-1-one (IRGACURE 1173 manufactured by CIBA SPECIALTY CHEMICALS), phenylethyl bromide, etc. Ketone compounds, benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, benzoin isobutyl ether, 2,2-dimethoxy-2-phenylacetophenone Benzene auxiliaries, such as CIGACURE 651 by CIBA SPECIALTY CHEMICALS, benzhydryl benzoic acid, methyl benzyl benzoyl benzoate, 4-phenyl diphenyl ketone, hydroxy diphenyl ketone, 4-phenyl Indole 4'-methyldiphenyl sulfide, 3,3'-dimethyl 4-methoxydiphenyl ketone (KAYACURE MBP, manufactured by Nippon Kayaku Co., Ltd.) Diphenyl ketone compound, thioxanthone, 2-chlorothiazinone (KAYACURE CTX manufactured by Nippon Kayaku Co., Ltd.), 2-methylthiaxanone, 2,4-dimethyl Xanthone (KAYACURE RTX, manufactured by Nippon Kayaku Co., Ltd.), isopropyl thioxanthone, 2,4-dichlorothiazinone (KAYACURE CTX, manufactured by Nippon Kayaku Co., Ltd.), 2,4- Thiopinone compounds such as diethyl thioxanthone (KAYACURE DETX manufactured by Nippon Kayaku Co., Ltd.) and 2,4-diisopropyl thioxanthone (KAYACURE DITX manufactured by Nippon Kayaku Co., Ltd.) Wait. The ultraviolet polymerization initiator is preferably 2-methyl 1-[4-(methylthio)phenyl]-2-N-morpholinylpropane-1 (IRGACURE 907 manufactured by CIBA SPECIALTY CHEMICALS), 1-hydroxyl ring Hexyl phenyl ketone (IRGACURE 184 manufactured by CIBA SPECIALTY CHEMICALS) or 2,2-dimethoxy 2-phenylacetophenone (IRGACURE 651 manufactured by CIBA SPECIALTY CHEMICALS). These photopolymerization initiators can be used singly or in an arbitrary ratio.

When a diphenyl ketone type compound and a thioxanthone type compound are used as a photopolymerization initiator, an auxiliary agent can also be used together in order to accelerate a photopolymerization reaction. Examples of the auxiliary agent include triethanolamine, methyldiethanolamine, triisopropanolamine, n-butylamine, N-methyldiethanolamine, diethylamineethyl methacrylate, and miscule. , 4'-diethylaminophenol, ethyl 4-dimethylaminobenzoate, 4-dimethylaminobenzoic acid (n-butoxy)ethyl ester, 4-dimethylaminobenzoic acid isoamyl ester, etc. Amine compound.

The amount of the photopolymerization initiator and the auxiliary agent added is preferably in a range which does not cause optical performance and flame retardancy of the polarizing plate, and is relative to the (meth)acrylate monomer 100 in the resin composition. The parts by mass are preferably from 0.5 to 12 parts by mass, preferably from 2 to 10 parts by mass. The auxiliary agent is preferably a photopolymerization initiator, and is preferably added in an amount of 0.5 to 2 times.

The resin composition may further contain a leveling agent. When the resin composition is applied to the protective layer or the polarizing element of the substrate by containing the leveling agent, the wettability on the substrate and the surface properties of the formed resin composition layer can be improved. As the type of the leveling agent, various compounds such as a lanthanoid, a fluorine-based, a polyether-based, an acrylic copolymer, and a titanate can be used. The amount of the leveling agent added is preferably 0.0001 to 10 parts by mass, preferably about 0.1 to 5 parts by mass, per 100 parts by mass of the (meth) acrylate monomer in the resin composition.

The resin composition may further contain a crosslinking agent. By containing a crosslinking agent, it is possible to improve the adhesion to the substrate after the resin composition is applied to the substrate and cured. As the kind of the crosslinking agent, various compounds such as an isocyanate type, a boron type, and a titanate type can be used. The amount of the crosslinking agent to be added is preferably 0.0001 to 20 parts by mass, preferably about 0.1 to 10 parts by mass, per 100 parts by mass of the (meth) acrylate monomer in the resin composition.

When the polymerizable monomer in the resin composition is a thermosetting type, the resin composition may further contain a polymerization initiator, a crosslinking agent, and/or a starting catalyst. As the type of the crosslinking agent, various conventional compounds such as an isocyanate type, a boron type, and a titanate type can be used. The amount of the crosslinking agent to be added is preferably 0.1 to 20 parts by mass, preferably about 1 to 10 parts by mass, per 100 parts by mass of the (meth) acrylate monomer in the resin composition.

[flame retardant layer (B)]

The flame-retardant layer (B) is a flame-retardant layer composed of a cured product of a resin composition containing a halogen-free flame retardant having one or more (meth) acrylonitrile groups contained in a predetermined amount. The halogen-free flame retardant having one or more (meth)acryl fluorenyl groups is contained in the resin composition in an amount of from 10 to 99.9% by mass, preferably from 15 to 75% by mass, preferably from 25 to 70% by mass. %, particularly preferably from 35 to 65 mass%. By using a halogen-free flame retardant having a (meth) acrylonitrile group, the performance of the flame-retardant layer can be improved and high flame retardancy can be achieved, and the optical performance substantially equal to that of the polarizing element can be maintained and maintained. Polarized plate. Specifically, the polarizing plate provided with the flame retardant layer can achieve good optical performance and excellent performance without causing deterioration of optical properties such as transmittance and polarization degree as compared with the polarizing plate before the flame retardant layer is provided. Flame retardant.

As the halogen-free flame retardant having one or more (meth) acrylonitrile groups, an organic phosphorus compound of a (meth) acrylate which is a part of the flame-retardant layer (A) described above can be used. A compound having a phosphaphenanthrene skeleton or a phosphazene skeleton is preferred. By using these halogen-free flame retardants, the performance of the flame retardant layer can be remarkably improved. Further, when the phosphazene skeleton is a cyclic triphosphazene skeleton, it is preferred because it can particularly enhance the flame retardancy function. The compound having a phosphaphenanthrene skeleton, a compound having a phosphazene skeleton, and a compound having a cyclic triphosphazene skeleton may be used singly or in combination of two or more kinds in any ratio.

<phosphorus phenanthrene compound>

The flame retardant having a phosphophenanthrene skeleton is preferably a compound having a 10-sided oxy-9-oxa-10-phosphaphenanthroline skeleton. A compound having a 10-sided oxo-9-oxa-10-phosphaphenanthroline skeleton is represented by the formula (1): The compound represented is preferred.

In the formula (1), R ₁ is preferably a (meth)acryl fluorenyl group or a substituent having a (meth) acryl fluorenyl group. The substitution position of the (meth)acryl fluorenyl group is preferably at the terminal end, but may be substituted at the side chain in the main chain of the substituent. The substituent having an acrylonitrile group is preferably the following formula: (n is an integer represented by 1 to 4, and m is a substituent represented by 0 or 1). The substituent having a methacrylinyl group is preferably the following formula: (n is an integer represented by 1 to 4, and m is a substituent represented by 0 or 1).

Specific examples of the compound represented by the formula (1) include compound examples PP-1 to PP-18, preferably compound examples PP-17 and compound examples PP-18.

<phosphazene compound>

The compound having a phosphazene skeleton is preferably a compound having a cyclic triphosphazene skeleton, and is preferably a compound having a 1,3,5,2,4,6-triazatriphosphorane skeleton. a compound having a 1,3,5,2,4,6-triazatriphosphorane skeleton, which is represented by the formula (2): The compound indicated is preferred.

In the formula (2), R ₂ to R ₇ may be the same or different, and each independently is, for example, a (meth)acryl fluorenyl group or a substituent having a (meth)acryl fluorenyl group. The substitution position of the (meth)acryl fluorenyl group is preferably at the terminal end, and is preferably substituted as a side chain in the main chain. The above-mentioned substituents S-1 to S-4 are preferred, and the substituents S-3 and the substituents S-4 are particularly preferred.

In a certain aspect, by using a compound having a phosphazene skeleton having a (meth) acrylonitrile group, it is possible to use a compound having a 10-sided oxy-9-oxa-10-phosphaphenanthrene skeleton. Achieve better optical performance and excellent flame retardancy.

The resin composition for producing the flame-retardant layer (B) is capable of using a polymerization initiator, an auxiliary agent, a crosslinking agent, and/or a starting catalyst to the above-mentioned flame retardant layer (A). The same amount of the same substance is further contained.

The flame-retardant layers (A) and (B) and (C) described below are capable of functioning as a plurality of layers constituting a general polarizing plate. For example, the flame-retardant layer can also be a layer which is generally referred to as a hard coat layer, or can be a monomer containing an alkyl acrylate as described in Japanese Patent No. 3410835 and Japanese Patent No. 3645005. An adhesive layer composed of a (co)polymer of the composition. In addition to the flame retardancy, the flame retardant layer can also have a layer having a separate function, and the number of laminated sheets of the film constituting the polarizing plate can be reduced, and the increase in the flammability due to an increase in the number of the film laminated sheets can be suppressed.

[flame retardant layer (C)]

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 a function of forming any layer of the flame-retardant polarizing plate. The flame retardant layer is preferably a layer which functions as a layer selected from the group consisting of an adhesive layer, an adhesive layer, and a hard coat layer. In addition to the flame retardancy, the flame retardant layer can reduce the number of laminated sheets of the film constituting the polarizing plate and suppress the increase in the flammability due to the increase in the number of laminated sheets of the film.

When the flame-retardant layer is also used as a layer constituting other layers of the polarizing plate, such as an adhesive layer, an adhesive layer, or a hard coat layer, it can be used as a monomer containing a matrix used for the production of the layer. The resin composition of the composition is produced by adding a compound having a phosphaphenanthrene skeleton and/or a compound having a phosphazene skeleton. Thereby, it is possible to provide the polarizing plate with excellent flame retardancy by adding only a small number of manufacturing steps. When the resin composition containing a compound having a phosphaphenanthrene skeleton and/or a phosphazene skeleton does not impair the optical properties and flame retardancy of the polarizing plate, it is possible to use a conventional layer constituting the polarizing plate. The resin composition is preferably a resin composition containing an acrylic monomer.

Hereinafter, the case where the flame-retardant layer is also suitable as the layer of the hard coat layer and the case where it is suitable as the layer of the adhesive layer will be described in detail.

Suitable for (C1) hard coating

The flame retardant layer suitable for the hard coat layer preferably contains at least 5 to 80% by mass of a compound having a phosphaphenanthrene skeleton and/or a compound having a phosphazene skeleton, and a phosphorus phenanthrene skeleton as described above. The compound and the aforementioned compound having a phosphazene skeleton are cured products of a resin composition of a different (meth) acrylate compound; or at least 10 to 99.9% by mass of a phenanthrene skeleton having a (meth) acryl fluorenyl group A cured product of a compound and/or a resin composition of a compound having a phosphazene skeleton having a (meth) acrylonitrile group. The resin composition can optionally further contain a polymerization initiator, an auxiliary agent, a crosslinking agent, and other components such as a leveling agent.

(a) a compound having a phosphaphenanthene skeleton and a compound having a phosphazene skeleton

(a1) a compound having a phosphaphenanthrene skeleton

The compound having a phosphaphenanthrene skeleton is preferably a "compound having a phosphaphenanthrene skeleton" as described in (a) a flame retardant layer (A) which is a halogen-free flame retardant.

(a2) a compound having a phosphazene skeleton

In order to particularly improve the flame-retardant function, a compound having a phosphazene skeleton is preferably a flame-retardant layer (A). (a) A halogen-free flame retardant has been described as having a phosphazene skeleton. compound of".

The compound having a phosphaphenanthrene skeleton and/or a compound having a phosphazene skeleton may be used singly or in combination of two or more kinds in any ratio. When the compound having a phosphaphenanthrene skeleton and/or the compound having a phosphazene skeleton does not have a (meth) acrylonitrile group, a compound having a phosphaphenanthene skeleton and/or a compound having a phosphazene skeleton in the resin composition The content is, for example, 5 to 80% by mass, preferably 15 to 75% by mass, preferably 25 to 70% by mass, more preferably 35 to 70% by mass. When the content of the compound having a phosphaphenanthrene skeleton and/or the compound having a phosphazene skeleton is within this range, it is possible to maintain high flame retardancy and impart adhesion and durability to the substrate. High surface hardness effect.

The compound having a phosphaphenanthrene skeleton and/or the compound having a phosphazene skeleton has a (meth) acrylonitrile group, and a compound having a phosphaphenanthene skeleton and/or a compound having a phosphazene skeleton in a resin composition For example, it is 10 to 99% by mass, preferably 15 to 80% by mass, preferably 25 to 70% by mass, more preferably 35 to 65% by mass. By setting the content of the compound having a phosphaphenanthrene skeleton having a (meth) acrylonitrile group and/or a compound having a phosphazene skeleton to such a range, it is possible to maintain high flame retardancy and impart The effect of adhesion, durability, and flexibility of the substrate.

(b) (meth) acrylate compound

The (meth) acrylate compound is a compound different from the compound having a phosphaphenanthrene skeleton and the phosphazene skeleton described above. The (meth) acrylate compound which does not contain a halogen and does not show flame retardance, which has been described in (a) a halogen-free flame retardant in the 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) acrylonitrile groups is preferably contained in the resin composition in an amount of 20 to 95% by mass in order to have sufficient physical strength by the flame retardant layer. It is preferably from 30 to 85% by mass, more preferably from 20 to 95% by mass. In order to obtain a flame retardant layer having a more sufficiently stable hardness and capable of improving the durability of the polarizing plate, a (meth) acrylate compound having three or more (meth) acrylonitrile groups is used in the resin composition. It is preferably from 20 to 95% by mass, preferably from 25 to 80% by mass, more preferably from 35 to 65% by mass. By using a resin composition containing 30% by mass or more of a (meth) acrylate compound having two or more acrylonitrile groups, since it is a layer generally called a hard coat layer, it is possible to obtain JIS in Japanese industrial specifications. A layer having a surface hardness of H or more as defined in K 5600-5-4 is preferred. The surface hardness of the flame retardant layer is preferably 2H or more, and particularly preferably 3H or more.

Further, part or all of the (meth) acrylate compound is preferably a (meth) acrylate compound having a hydroxyl group in the molecule. By mixing a (meth) acrylate compound having a hydroxyl group in the resin composition, the adhesion between the flame-retardant layer and the polarizing element can be further improved. In particular, when a cellulose-based film, in particular, cellulose triacetate (TAC) and other transparent cellulose acetate-based films are used as a protective layer of a polarizing element, the adhesion between the protective layer and the flame-retardant layer of the polarizing element can be improved. Sex is especially good. The content of the (meth) acrylate compound having a hydroxyl group is, for example, 20 to 90% by mass in the resin composition, preferably 30 to 80% by mass, preferably 40 to 70% by mass, more preferably 45 to 5%. 65% by mass.

Examples of the (meth) acrylate compound having a hydroxyl group in the molecule include those described in (a) a flame retardant layer (A) which does not contain a halogen.

The compounding ratio of the compound having a phosphaphenanthene skeleton and/or a compound having a phosphazene skeleton to a (meth) acrylate compound which does not exhibit halogen resistance and exhibits flame retardancy is a mass ratio of 5:94 to 80:19. It is better. By setting the blending ratio to this range, it has an effect of improving flame retardancy, hardness, and durability. In particular, when the compound having a phosphaphenanthrene skeleton and/or the compound having a phosphazene skeleton has two or more (meth) acrylonitrile groups, the above-mentioned compounding ratio is a mass ratio of 10:88 to 75:28 because It is preferable to further improve the flame retardancy and further improve the hardness and durability. It is preferably from 20:78 to 70:28, more preferably from 30:68 to 65:33, and particularly preferably from 35:63 to 65:33.

(c) other ingredients

The resin composition can further contain a polymerization initiator which has been described in the (flame retardant layer (A)] (a) halogen-free flame retardant.

The resin composition may further contain a leveling agent described in (a) a flame retardant layer containing no halogen in the flame retardant layer (A).

The resin composition may further contain a crosslinking agent which has been described in (a) a flame retardant layer which does not contain a halogen in the flame retardant layer (A).

When the polymerizable monomer in the resin composition is a thermosetting type, the resin composition may further contain (a) a flame retardant layer (A) in which the halogen-free flame retardant has been described. Agent, crosslinker and/or starting catalyst.

Examples of the method for forming the flame-retardant layers (A), (B), and (C) include a coating liquid obtained by diluting a resin composition directly or by using a suitable solvent, and coating. The protective layer or the polarizing element is then subjected to a method of removing the solvent by heating or the like, and hardening it by heating or 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 coating, and does not cause surface deterioration. Examples of the solvent for dilution include water, aromatic hydrocarbons such as toluene and xylene, and anisole and Ethers such as alkane and tetrahydrofuran, methyl isobutyl ketone, methyl ethyl ketone, cyclohexanone, cyclopentanone, 2-pentanone, 3-pentanone, 2-hexanone, 3-hexanone, 2- Ketones such as heptanone, 3-heptanone, 4-heptanone, 2,6-dimethyl 4-heptanone, alcohols such as n-butanol, 2-butanol, cyclohexanol, and isopropanol, methyl Cyrus, methyl acetate, Susie, etc., ethyl acetate, butyl acetate, methyl lactate, propylene glycol monomethyl acetate, propylene glycol ethyl ether acetate, methoxyethyl acetate, acetic acid An ester such as ethoxyethyl ester, dimethyl hydrazine, acetonitrile or N,N-dimethylacetamidine, but is not limited thereto. Preferably, toluene, cyclopentanone, and ethyl acetate are preferred. Further, the solvent may be used singly or in combination of two or more kinds. The concentration of the total solid content of the coating liquid varies depending on the solvent solubility, the wettability on the substrate to be coated, and the thickness after coating, and is preferably 5 to 95% by mass. Preferably, it is about 10 to 80% by mass.

As a method of forming the flame retardant layer, the resin layer can be provided on the substrate of the protective layer, the protective film, or a layer such as a polarizing element by coating. It may be a method of previously coating a film on another film, and then transferring or laminating the hardened layer to a substrate such as a protective layer or a polarizing element. The layer may be provided by a method of directly coating a polyvinyl alcohol-based film or the like which adsorbs a dichroic dye and boric acid. Alternatively, it may be applied not only to a protective layer or a polyvinyl alcohol-based film which adsorbs a dichroic dye, but may be previously coated on another film, and then the cured layer may be transferred or laminated to a protective layer or polarized light. A substrate such as a device or a polyvinyl alcohol-based film that adsorbs a dichroic dye. Further, the method of providing a layer while providing an adhesive layer is also excellent in efficiency, and further, the adhesive layer itself is a resin composition, and the polarizing plate having a flame retardant layer can be produced most easily. The coating method is not particularly limited, and examples thereof include a spin coating method, a bar coating method, a gravure coating method, a micro gravure coating method, a calender coating method, a spray coating method, and a liquid surface bending coating method. The method of cloth and so on.

The hardened layer obtained by hardening the resin composition is preferably sufficiently polymerized by heating or ultraviolet irradiation, and the amount of unreacted is extremely small. The degree of the unreacted acrylate compound in the resin composition after hardening is preferably from 0 to 5% by mass, preferably from 0 to 3% by mass, more preferably from 0 to 1% by mass. In order to obtain a hardened layer which is sufficiently cured, for example, the thickness of the resin composition layer after coating is optimized, and the type and amount of the photopolymerization initiator to be added are optimized, and sufficient heating or ultraviolet irradiation is applied. In the inert gas such as nitrogen, the environment at the time of ultraviolet irradiation is changed to be hardened. Among these, since the thickness of the resin layer is optimized, it can be carried out only by changing the resin concentration and the resin coating amount, and is the easiest.

The thickness of the flame-retardant layer obtained by curing the resin composition is from 0.1 to 100 μm, preferably from 0.5 to 10 μm, preferably from 1 to 8 μm, more preferably from 2 to 6 μm. When it is thicker than 100 μm, the residual unreacted monomer increases and the wet heat durability is insufficient, and the polarizing plate becomes red in the dry heat durability test. When the layer is thinner than 0.1 μm, on the contrary, the improvement in moist heat durability cannot be achieved. The amount of ultraviolet light to be irradiated varies depending on the type of the acrylate compound, the type and amount of the photopolymerization initiator, and the film thickness, and is preferably, for example, about 100 to 1,500 mJ/cm ² .

Further, it is preferred that the obtained flame retardant layer be transparent even if it is treated with an alkaline solution. Specifically, after the alkali aqueous solution of pH 11 or more is treated at 40 ° C for 10 minutes or more, white turbidity is not produced as one of the indexes. In this reference, a film in which a layer of a UV-curable resin composition is applied to a polyethylene terephthalate film and cured in a thickness of 5 μm is provided, and is treated with an aqueous solution of pH 11 at 40 ° C. More than a minute, the light transmittance at a wavelength of 550 nm is preferably 85% or more, and more preferably 90% or more. In addition, it is preferred that the flame retardant layer obtained by curing the resin composition is treated with an aqueous alkali solution to make the flame retardant layer hydrophilic and to improve the adhesion to the polyvinyl alcohol film. As an indicator of the hydrophilicity at this time, the contact angle at the time of 10 μL of water drop is 60° or less, preferably 50° or less, more preferably 40° or less. When the flame-retardant layer is bonded to the polarizing element, it is possible to suitably use a flame-retardant layer which is treated with an aqueous alkali solution after hardening and neutralized in water or an acidic aqueous solution, followed by drying.

(C2) suitable for the adhesive layer

The flame retardant layer suitable for the adhesive layer can be formed by polymerizing or copolymerizing an adhesive resin composition containing a compound having a phosphaphenanthrene skeleton and/or a compound having a phosphazene skeleton. In the adhesive resin composition or a layer obtained by using the same, a compound having a phosphaphenanthrene skeleton of 5 to 80% by mass and/or a compound having a phosphazene skeleton is imparted with flame retardancy. It is also preferable because it is also highly transparent and can be attached. It is preferably from 10 to 70% by mass, more preferably from 12 to 50% by mass, particularly preferably from 14 to 35% by mass, because it maintains high durability while maintaining high flame retardancy at a high level. good.

As a compound having a phosphaphenanthrene skeleton and/or a compound having a phosphazene skeleton, it is possible to contain a resin for an adhesive layer at the same level as the compound of the same kind as described above when it is suitable for a (C1) hard coat layer. The composition (hereinafter also referred to as "resin composition for adhesive layer" or "adhesive resin composition"), or may be a copolymerized component contained in the adhesive resin composition, and has a phenanthroline skeleton (meth) acrylate, or a (meth) acrylate compound having a phosphazene skeleton.

The adhesive resin composition is preferably a (meth) acrylate compound, particularly an acrylate alkyl ester as an adhesion-imparting agent. The adhesive resin composition may contain, in addition to the acrylic alkyl ester, a polymerizable monomer having a hydroxyl group, a polymerizable monomer having a mercapto group, a polymerizable monomer having a carboxyl group, and/or not having Further monomer component such as a polymerizable monomer of a functional group. The adhesive resin composition preferably contains at least two or more kinds of acrylic alkyl esters, or at least one or more acrylic acrylates and one or more further monomer components.

Preferred acrylic alkyl esters are, for example, selected from the group consisting of methyl (meth)acrylate, ethyl (meth)acrylate, isopropyl (meth)acrylate, n-propyl (meth)acrylate, (meth)acrylic acid. One of a group consisting of isobutyl ester, n-butyl (meth)acrylate, tert-butyl (meth)acrylate, and (meth)acrylic acid C1 to 12 alkyl ester Separate or a combination of two or more. Preferably, the acrylic alkyl ester is one or more selected from the group consisting of n-butyl (meth)acrylate, tert-butyl (meth)acrylate, and methyl (meth)acrylate. combination. In particular, the acrylic alkyl ester is selected from the group consisting of a combination of n-butyl (meth)acrylate and a third butyl (meth)acrylate, or n-butyl (meth)acrylate or t-butyl (meth)acrylate. When it is combined with methyl (meth) acrylate, it is preferable because durability is particularly good. Here, "(meth)acrylic acid" means acrylic acid and/or methacrylic acid.

The content of the acrylic alkyl ester-based monomer in the adhesive resin composition is preferably from 50 to 100% by mass, preferably from 70 to 95% by mass. When the content of the alkyl acrylate is 50% by mass or more, the solubility of the component of the phosphaphenanthene skeleton or the phosphazene skeleton and/or the (meth) acrylate compound thereof can be improved, and the precipitation of the compound can be suppressed. The penetration rate is low. Moreover, even when exposed to high temperature, high humidity, and high intensity light, the adhesive layer obtained from the adhesive resin composition is less likely to be deteriorated, for example, due to foaming and minute defects, phenanthroline skeleton or phosphorus. The composition of the nitrile skeleton or the precipitation of the (meth) acrylate compound or the like is low in adhesion to glass, a film, or the like, and the transparency is lowered, and the optical film provided with the adhesive layer can be reduced in discoloration, white turbidity, and physical damage. Deterioration of etc.

Examples of the polymerizable monomer having a hydroxyl group contained in the adhesive resin composition include 2-hydroxyethyl acrylate, 2-hydroxyethyl methacrylate, 2-hydroxypropyl acrylate, and methacrylic acid. 2-hydroxypropyl ester, 3-chloro-2-hydroxypropyl acrylate, 3-chloro-2-hydroxypropyl methacrylate, etc. (meth)acrylic acid hydroxy C1 to 5 alkyl ester, diethylene glycol monoacrylate, And diethylene glycol (meth) acrylate such as diethylene glycol monomethacrylate, and examples thereof include epoxidized methacrylate and allyl epoxypropyl ether. The content of the polymerizable monomer having a hydroxyl group in the adhesive resin composition is preferably 0.5 to 7 parts by mass, preferably 0.8 to 4.3 parts by mass, per 100 parts by mass of the alkyl acrylate. By including a polymerizable monomer having a hydroxyl group, the transparency of the adhesive layer obtained from the adhesive resin composition can be further improved, and the adhesive layer and the flame retardant polarizing plate having the same can be further improved for high temperature and high temperature. Durability of humidity and high intensity light.

As a polymerizable monomer which preferably has a mercapto group in the adhesive resin composition, for example, N,N-dimethylaminopropyl acrylamide, N,N-dimethyl decylamine can be mentioned. An acrylamide-based monomer such as N,N-diethylacrylamide, propylene decylmorpholine, N-isopropylacrylamide, N-methylol acrylamide or acrylamide. The content of the polymerizable monomer having a guanamine group in the adhesive resin composition is preferably from 0.5 to 29 parts by mass, preferably from 3 to 21 parts by mass, per 100 parts by mass of the alkyl acrylate. By containing a polymerizable monomer having a mercapto group, the transparency of the adhesive layer obtained from the adhesive resin composition can be improved, and the adhesive layer and the flame retardant polarizing plate having the same can be further improved for high temperature. Durability of high humidity and high intensity light exposure.

Examples of the polymerizable monomer having a carboxyl group contained in the adhesive resin composition include acrylic acid, methacrylic acid, maleic acid, and itaconic acid. A polymerizable monomer having a carboxyl group is contained in a monomer composition in combination with a polymerizable monomer having a mercapto group, and does not inhibit mutual compatibility and does not form an adhesive layer composed of an adhesive resin composition. The transparency is low, but it is better. The content of the polymerizable monomer having a carboxyl group in the resin composition for adhesion is preferably 0.5 to 7 parts by mass, preferably 1 to 4.3 parts by mass, per 100 parts by mass of the alkyl acrylate. By containing a polymerizable monomer having a carboxyl group in the above range, the ultraviolet absorber can be made to have a higher concentration while suppressing the lowering of the transmittance of the adhesive layer, and even at high temperature, high humidity, and high intensity light irradiation. Under the circumstance, it is also possible to suppress the deterioration of the adhesive layer, for example, to further improve the effect of suppressing the transparency and the adhesion with a low period of time.

Examples of the polymerizable monomer which does not have a functional group contained in the 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 from 0 to 43 parts by mass based on 100 parts by mass of the alkyl acrylate. By containing a polymerizable monomer having no functional group, the adhesion of the adhesive layer is improved, the transparency is improved, the adhesion at low temperature and high temperature is improved, and the surface properties at the time of coating are improved. .

The adhesive resin composition contains 100 parts by mass of an alkyl acrylate, 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 a guanamine group, because it is further difficult to further improve The durability of the flammable polarizer is particularly good. The adhesive resin composition can further suppress the adhesion rate of the adhesive layer by further containing 0.5 to 7 parts by mass of the polymerizable monomer having a carboxyl group, even if the phosphaphenanthrene compound and/or the phosphazene compound are brought to a higher concentration. In addition, it is possible to obtain an adhesive resin composition capable of suppressing deterioration even under high-temperature, high-humidity, and high-intensity light irradiation conditions, for example, further suppressing, for example, transparency and adhesion for a long period of time.

As the monomer component contained in the adhesive resin composition, a monomer composition containing an acrylic alkyl ester described in Japanese Patent No. 3410835 and Japanese Patent No. 3645005 can be used.

The adhesive layer can be produced by dissolving an adhesive resin composition in an organic solvent and copolymerizing a radical in an organic solvent by a usual method. Examples of the organic solvent used for the polymerization include aromatic hydrocarbons such as toluene and xylene, esters such as ethyl acetate and butyl acetate, and aliphatic alcohols such as n-propanol and isopropanol, and Ketones such as ketoethyl ketone and methyl isobutyl ketone. Examples of the polymerization catalyst used in the radical polymerization include azobisisobutyronitrile, benzoyl peroxide, di-tert-butyl peroxide, and cumene peroxide which are common polymerization catalysts. Hydrogen, etc.

The copolymer obtained from the adhesive resin composition or the composition thereof contains a monomer unit based on each monomer contained in the adhesive resin composition, and the content of each monomer unit corresponds to the monomer. The content of each monomer of the composition. Therefore, the acrylic copolymer resin preferably contains 50 to 100% by mass of the acrylic alkyl ester-based monomer unit, and is arbitrarily selected to be further preferably contained with respect to 100 parts by mass of the acrylic alkyl ester-based monomer unit. It is 0.5 to 7 parts by mass based on the monomer unit of the hydroxyl group-containing polymerizable monomer, preferably 0.5 to 29 parts by mass based on the monomer unit having a mercapto group-containing polymerizable monomer, preferably 0.5 to 7 The monomer unit based on the polymerizable monomer having a carboxyl group, and/or preferably from 0 to 43 parts by mass based on the monomer unit of the polymerizable monomer having no functional group.

The glass transition temperature (hereinafter, abbreviated as Tg) of the cured product of the adhesive resin composition is preferably -20 ° C or lower, preferably -30 ° C to -60 ° C, and further preferably, the weight average molecular weight is 500,000 to 2,000,000, preferably It is 700,000 to 1,600,000. When the Tg is more than -20 ° C, there is a case where the adhesion is insufficient and the durability is poor. Further, when the weight average molecular weight is less than 500,000, there is a possibility that the heat resistance is insufficient, and when it exceeds 2,000,000, the adhesion is insufficient, and peeling or the like is likely to occur.

<film thickness>

When the film thickness of the flame retardant layer is between 0.1 and 100 μm, the flame retardancy is exhibited, but the hard coat layer is, for example, 0.5 to 20 μm, preferably 0.5 to 15 μm, more preferably 1 to 10 μm. good. The adhesive layer is, for example, 5 to 100 μm, preferably 8 to 50 μm, preferably 10 to 40 μm, and most preferably 15 to 30 μm. In the adhesive layer, it is also possible to laminate such a flame-retardant layer with other adhesive layers, or to further laminate a layer having flame retardancy, although it is a plurality of layers but used as an adhesive layer.

<flammable polarizer>

The flame-retardant layer can be provided as a polarizing plate, and can exhibit flame retardancy, but particularly on the surface side of the polarizing element, for example, on the surface layer, the adhesive layer, or any layer of the adhesive layer, particularly The layer layer is preferably not only capable of imparting "non-combustible" but also imparting "non-combustible" performance, and not only protects the polarizing element but also maintains its optical characteristics, and does not burn as a polarizing plate from the surface layer.

The flame-retardant polarizer is provided with a polarizing element and a flame-retardant layer provided on one or both sides of the polarizing element. The flame retardant polarizing plate is arbitrarily provided with a further layer such as a protective layer, a pressure-sensitive adhesive layer, a retardation film, an adhesive layer, a surface flaw preventing layer, and an anti-glare 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.

In some cases, the flame retardant layer (A), (B), or (C) described above is used as the flame retardant layer. When the flame-retardant layer is provided on both sides of the polarizing element, the flame-retardant layer of one aspect is attached to one surface, and the flame-retardant layer of another aspect may be provided on the other surface.

As the polarizing element, a polarizing element which is usually used by a user and preferably flammable can be used. The polarizing element is impregnated with iodine or dichroism by, for example, a film formed of a polyvinyl alcohol-based resin such as polyvinyl alcohol, polyvinyl acetal, polyvinyl acetal or ethylene-vinyl acetate copolymer saponified product. A dichroic dye such as a dye, and a film obtained by imparting a polarizing property by using boric acid or the like as a crosslinking agent.

In addition, as a polarizing element, it is described in Japanese Patent Laid-Open No. Hei 8-190016, No. Hei 11-119023, No. Hei 11-218611, and Japanese Patent No. 4360100. By.

Further, a polarizing element having a polyene structure in which a polyvinyl alcohol is dehydrated and reacted, and a polarizing element is provided on a resin substrate, as described in Japanese Patent No. 3001984 and Japanese Patent No. 4269939, A polarizing element such as Japanese Patent No. 4,275,691 and Japanese Patent No. 4,275,692.

It is preferable to further provide a plastic film having excellent transparency, mechanical strength, thermal stability, moisture shielding property, or the like as a protective layer on one or both sides of the polarizing element. Examples of the plastic having excellent transparency, mechanical strength, thermal stability, moisture shielding property, and the like include a polyester resin, a cellulose resin, an acetate resin, a polyether oxime resin, and a polycarbonate. A thermoplastic resin such as a resin, a polyamide resin, a polyimide resin, a polyolefin resin, or an acrylic resin, and an acrylic, urethane, urethane, or epoxy resin. And thermosetting resins such as anthrone and ultraviolet curable resins. The polyolefin-based resin may be an amorphous polyolefin-based resin and a resin having a polymerization unit of a cyclic polyolefin such as a norbornene or a polycyclic norbornene-based monomer. Further, on one or both sides of the polarizing element, in addition to the above-mentioned plastic film, a cellulose-based protective layer may be provided instead of the plastic film. As the cellulose-based protective layer, a cellulose-based film, in particular, cellulose triacetate can be usually used.

The flame retardant polarizing plate may further include a hard coat layer such as an adhesive layer, an adhesive layer, a surface flaw preventing layer, and an anti-glare layer, and/or a retardation film, and these layers can be used as a general user. For example, as the retardation film, a film obtained by stretching a film made of a resin such as polyvinyl alcohol, polycarbonate, or cycloolefin can be suitably used to impart phase difference, or coated with A film having a liquid crystal substance or a film having the layer. In the flame retardant polarizing plate, the retardation film is preferably laminated on a polarizing element, a protective layer or the like. The retardation film may be provided on a layer such as a flame retardant layer or a pressure-sensitive adhesive layer. Further, the adhesive layer is made of a usual adhesive, preferably an acrylic adhesive, for example, acrylic acid obtained from an acrylic alkyl ester monomer described in Japanese Patent No. 3410835 and Japanese Patent No. 3645005. A polymer resin or an anthrone-based adhesive is formed. The adhesive layer may be disposed directly in contact with the polarizing element or the phase difference plate, or may be disposed on the polarizing element or the phase difference plate via other layers. The adhesive layer is preferably the outermost layer provided on one side or both sides of the flame-retardant polarizing plate.

In the flame-retardant polarizer, the flame-retardant layer can be provided with flame retardancy at any position, and the flame-retardant layer is preferably provided in the environment of the polarizing element via an arbitrary protective layer (protective film) and other layers. On the exposed side and/or the exposed side of the light source, such a layer is preferably provided on both the exposed side of the polarizing element and the side of the exposed side of the light source. Further, the position of the flame-retardant layer is preferably the outermost layer on the side of the exposed surface of the environment and/or the side of the exposed surface of the light source. The exposed surface of the environment or the exposed surface of the light source is directly exposed to external important factors such as light, heat, humidity, rushing, and fire. Specifically, in the liquid crystal display, on the side of the environmentally exposed surface, the polarizing plate is usually bonded to both sides of the liquid crystal cell, and the polarizing plate is attached to the viewer side of the liquid crystal cell, and the flame retardant layer is disposed on the polarizing element. It is closer to the observer side, that is, it is provided in such a manner as to be disposed on the side of the exposed surface side of the polarizing element. When it is exposed to external light by being placed on the exposed side of the environment, it is possible to suppress not only discoloration due to heat generation, but also to provide "non-combustible" and "not easy to burn" polarizing plates even when a fire is generated. When the polarizing plate is attached to both sides of the liquid crystal cell, the light source is exposed on the side of the light source, which is commonly referred to as a flame-retardant layer on the backlight side, and when a strong light such as a projector is irradiated to the polarizing plate, The flame retardant layer is placed on the side illuminated by the light. In particular, when it is known that it is irradiated with light such as a lens of a projector or the like, or when it is irradiated with light having a strong intensity, it may be heated to a high temperature depending on the intensity of the light, and may be burned. From such an exposed surface of the light source, it is possible to prevent the phenomenon of burning or burning due to important factors such as light, heat, and fire.

The flame retardant layer is especially a layer disposed on the side of the exposed surface of the environment, such as an adhesive layer and/or a hard coat layer, because it is not only "not easy to burn" performance (flammability), but also can improve "non-combustible" Performance (non-combustible) is preferred.

As a preferable specific configuration of the flame-retardant polarizing plate, for example, an 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/phase difference plate/adhesive layer, FR layer/protective layer/polarizing element/protective layer/PSA layer/phase difference plate/FR layer/adhesive layer, FR layer/ Protective layer / polarizing element / protective layer / FR layer / PSA layer / phase difference 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/polarizing element/protective layer/FR layer, and FR layer/protective layer/polarizing element/protective layer/FR layer/PSA layer/FR layer/protective layer/polarizing element/protective layer/FR layer and the like.

Preferred examples of the polarizing plate include an FR layer/protective layer/polarizing element/protective layer, an FR layer/protective layer/polarizing element/protective layer/FR layer, an FR layer/protective layer/polarizing element/protective layer/ Phase difference plate / adhesive layer, FR layer / protective layer / polarizing element / protective layer / PSA layer / phase difference plate / FR layer / adhesive layer, FR layer / protective layer / polarizing element / protective layer / FR layer / PSA layer / Phase difference plate/adhesive layer, FR layer/protective layer/polarizing element/protective layer/PSA layer/protective layer/polarizing element/protective layer/FR layer, and FR layer/protective layer/polarizing element/protective layer/FR layer/ PSA layer / FR layer / protective layer / polarizing element / protective layer / FR layer.

The preferred composition of the polarizing plate is FR layer/protective layer/polarizing element/protective layer/FR layer, FR layer/protective layer/polarizing element/protective layer/phase difference plate/FR layer/adhesive layer, FR layer/protective layer/ Polarizing element / protective layer / FR layer / PSA layer / phase difference plate / adhesive layer, and FR layer / protective layer / polarizing element / protective layer / FR layer / PSA layer / FR layer / protective layer / polarizing element / protective layer / In the case of the FR layer, the flame retardancy can be particularly improved.

In general, on the surface of the polarizing plate, in addition to the hard coat layer, an anti-glare layer (hereinafter also referred to as "AG layer"), an anti-reflection layer (hereinafter also referred to as "AR layer"), and a low-reflection layer (hereinafter, Also known as the "LR layer". The AG layer is such that the surface of the polarizing plate contains a resin composition and an inorganic filler such as cerium oxide, aluminum or titanium, or an organic filler containing an acrylic resin, polystyrene or the like, and is coated on the surface of the film or the surface of the substrate. The fine concavities and convexities are formed to prevent the layer of glare (Glare). Since the AG layer is a layer formed of a mixture of a filler and a resin composition, it is also possible to contain a halogen-free flame retardant, particularly a compound having a phosphaphenanthrene skeleton or a phosphazene skeleton, in the resin composition. Play a strong flame retardant. The AR layer is formed of a material having a different refractive index, specifically, a multilayer film of titanium oxide, zinc oxide, acidified cerium oxide, magnesium oxide, aluminum oxide, or the like, by using a low refractive index layer and a high refractive index layer. The layering is designed to prevent the reflection layer from being generated at the interface by mutually reflecting the reflected light generated at each interface. This layer is mostly composed of 2 to 4 layers. The purpose of the LR layer is to reduce the reflection of the interface and apply a low refractive index material (single layer) to reduce the reflectance. However, the thickness of the AR layer and the LR layer is usually 0.2 μm or less, and even if such a layer of 0.2 μm or less is on the surface of the polarizing plate, it does not affect the flame retardancy. Therefore, it is possible to have an AR layer and/or an LR layer, and it is also possible to achieve the flame retardancy of the polarizing plate.

The flame-retardant polarizing plate of the present invention can satisfy the flammability test FMVSS 302 of the automobile interior material in the United States, and therefore can satisfy the flame retardancy and the refractory property of the interior decoration required for the automobile. Here, FMVSS (Federal Motor Vehicle Safety Standard) is a specification prescribed by the National Highway Traffic Safety Administration.

Specifically, in the FMVSS 302, a test piece having a size of 102 mm × 356 mm was placed at 21 ° C and 50% RH for 24 hours, and then the flame height was set to 38 mm, and the flame was brought into contact with the flame 15 at a position of 19 mm from the center of the end portion. second. It is required that the burning speed of the contact flame must be 102 mm/min or less, or the burning distance from the burning time measuring line must be within 51 mm and must be extinguished within 60 seconds.

The polarizing plate of the present invention can maintain transparency and adhesion and has high durability even under conditions of contact with flame, high temperature, high humidity, or exposure to high-intensity light for a long period of time. Moreover, the height of the flame retardancy is such that it can satisfy the flammability test FMVSS 302 of the automobile interior materials in the United States, and the use of such characteristics makes it possible to have high durability and reliability in applications requiring flame retardancy and refractory burnability. The use of a high liquid crystal display is useful, and is particularly useful for display applications such as vehicle applications, various industrial meters, and household electrical products.

 [Examples]  

Hereinafter, the present invention will be specifically described by way of Examples and Comparative Examples, but the present invention is not limited thereto.

[Example 1]

(1) Manufacture of a protective layer (TAC) having an FR layer

40 parts by mass of pentaerythritol hexaacrylate (Kanato PET-30), 60 parts by mass of 2,2,4,4,6,6-lu[2-(methacryl oxime) Oxy)ethoxy]-1,3,5,2,4,6-triazatriphosphorane (produced by Idemitsu Petrochemical Co., Ltd., PPZ monomer), 5 parts by mass of IRGACURE 184 (manufactured by CIBA SPECIALTY CHEMICALS) And 82 parts by mass of 2-butanone and 18 parts by mass of cyclopentanone were mixed to prepare a resin composition. The resin composition was applied to a cellulose triacetate film (TAC) having a film thickness of 60 μm by using a bar coater ROD #6 (manufactured by TESTER Industries, Inc.) and having a film thickness of 5 μm after solvent drying (BRIGHT Corporation) , P980GL), and dried at 70 ° C for 2 minutes. The dried coating film was irradiated with ultraviolet rays using a high-pressure mercury lamp (accumulated light amount: 400 mJ/cm ² ) in the air to produce an FR layer. Two sets of TACs having the FR layer were fabricated. The aqueous solution adjusted to pH 11 with sodium hydroxide was used, and the TAC having the obtained FR layer was immersed in the aqueous alkali solution for 10 minutes to reduce the contact angle of water on the surface of the TAC film from 80.0° to 52.3°.

(2) Manufacturing of polarizing elements

A polyvinyl alcohol film (manufactured by Kuraray Co., Ltd., VF-PS #7500) having a saponification degree of 99% or more and a film thickness of 75 μm was immersed in warm water at 40 ° C for 2 minutes to carry out a swelling treatment. The swelled film was immersed in a 45 ° C aqueous solution of the formulated coloring matter described in Example 1 of JP-A-11-218611, for 3 minutes, and the dye was adsorbed. The film on which the dye was adsorbed was washed with water, washed, and then treated with an aqueous solution containing 2% by mass of boric acid at 40 ° C for 1 minute. The film obtained by the boric acid treatment was treated for 5.0 minutes in an aqueous solution containing 3.0% by mass of boric acid at 55 ° C while extending 5.0 times. While the film obtained by treating the boric acid was kept in a state of tension, it was subjected to a water washing treatment at 30 ° C for 15 seconds. The obtained film was immediately dried at 70 ° C for 9 minutes to obtain a polarizing element having a film thickness of 28 μm.

(3) Manufacture of polarizing plates

The TAC surface of the TAC film having the FR layer in the two groups after the alkali treatment was adhered to each other using a polyvinyl alcohol aqueous solution (a polyvinyl alcohol (manufactured by VAM & POVAL Co., Ltd., NH-26) 4% by mass aqueous solution). On both surfaces of the obtained polarizing element, a polarizing plate in which these elements are laminated is produced in the following order: FR layer/TAC/polarizing element/TAC/FR layer.

(4) Evaluation of transparency and polarization

The polarizing element before bonding with the TAC having the FR layer manufactured by "(2) Manufacturing of polarizing element" and the monomer transmittance and the degree of polarization of the obtained polarizing plate were measured. The monomer transmittance and the degree of polarization were obtained by using V-7100 manufactured by JASCO Corporation. The polarizing element had a monomer transmittance of 38.0% and a degree of polarization of 99.9% or more. Similarly to the polarizing element, the polarizing plate has a monomer transmittance of 38.0% and a degree of polarization of 99.9% or more. Therefore, the polarizing plate having the TAC having the FR layer showed no difference in transmittance from the polarizing element.

(5) Flame retardancy test

When the obtained polarizing plate was evaluated in accordance with the fuel economy test of the Federal Motor Vehicle Safety Standard (FMVSS 302), the burning rate was 102 mm/min or less, and it was confirmed that the polarizing plate satisfying the standard was obtained.

[Embodiment 2]

Two sets of TAC having an FR layer were produced in the same manner as in (1) of Example 1. Two polarizing elements were produced in the same manner as (2) of Example 1 except that the adsorption time of the dye was changed from 3 minutes to 1 minute and 30 seconds. The TAC surface of the TAC having the FR layer was bonded to one surface of the polarizing element, and a separate TAC was bonded to the other surface of the polarizing element to fabricate two sets of FR layers/TAC/polarizing elements/TAC. For the lamination, an aqueous solution of polyvinyl alcohol (a 4% by mass aqueous solution of polyvinyl alcohol (manufactured by VAM & POVAL, Japan, NH-26)) was used. An adhesive layer having a thickness of 22 μm was placed between the two groups of the FR layer/TAC/polarizing element/TAC TAC surface using an adhesive (PTR-3000 manufactured by Nippon Kayaku Co., Ltd.) to bond the TAC surfaces. The polarizing plates in which the elements are laminated are manufactured in the following order: FR layer/TAC/polarizing element/TAC/adhesive layer/TAC/polarizing element/TAC/FR layer.

When the obtained polarizing plate was applied to the flammability test of FMVSS 302, the burning speed in the extending direction of the polarizing element was 71.9 mm/min, and the burning speed in the non-extension direction of the polarizing element was 39.7 mm/min, according to FMVSS. The predetermined burning rate was 102 mm/min or less, and it was confirmed that the polarizing plate satisfying the standard was obtained.

[Example 3]

Four sets of TACs having an FR layer were produced in the same manner as in (1) of Example 1. Two polarizing elements were produced in the same manner as in (2) of the first embodiment except that the adsorption time of the dye was changed from 3 minutes to 1 minute and 30 seconds.

Two sets of TAC surfaces of the TAC having the FR layer were bonded to both surfaces of the polarizing element to produce two sets of the F layer/TAC/polarizing element/TAC/FR layer. For the lamination, an aqueous solution of polyvinyl alcohol (a 4% by mass aqueous solution of polyvinyl alcohol (manufactured by VAM & POVAL, Japan, NH-26)) was used. An adhesive layer having a thickness of 22 μm was placed between the FR layers of the two groups of the F layer/TAC/polarizing element/TAC/FR layer using an adhesive (PTR-3000 manufactured by Nippon Kayaku Co., Ltd.) to sandwich the FR layers. For bonding, a polarizing plate in which these elements are laminated is manufactured in the following order: FR layer/TAC/polarizing element/TAC/FR layer/adhesive layer/FR layer/TAC/polarizing element/TAC/FR layer.

When the obtained polarizing plate was applied to the flammability test of FMVSS 302, the burning rate was 102 mm/min or less, and it was confirmed that the polarizing plate satisfying the standard was obtained.

[Example 4]

In addition to the TAC film having the FR layer produced in Example 2, 50 parts by mass of 50 parts by mass of neopentyl alcohol hexaacrylate (KAYARAD PET-30 manufactured by Nippon Kayaku Co., Ltd.) was used as the resin composition. Halogen-containing and flame retardant 2,2,4,4,6,6-lu[2-(methacryloxy)ethoxy]-1,3,5,2,4,6-tri Other than the point of the resin composition prepared by mixing a mixture of azatriphosphorus benzene, 5 parts by mass of IRGACURE 184 (manufactured by CIBA SPECIALTY CHEMICALS), 82 parts by mass of 2-butanone, and 18 parts by mass of cyclopentanone The polarizing plate was produced in the same manner.

When the obtained polarizing plate was applied to the flame resistance test of FMVSS 302, the burning rate was 102 mm/min or less, and it was confirmed that a polarizing plate satisfying the standard was obtained.

[Example 5]

In addition to the TAC film having the FR layer produced in Example 2, 60 parts by mass of pentaerythritol hexaacrylate (KAYARAD PET-30 manufactured by Nippon Kayaku Co., Ltd.) and 40 parts by mass were used as the resin composition. Halogen-containing and flame retardant 2,2,4,4,6,6-lu[2-(methacryloxy)ethoxy]-1,3,5,2,4,6-tri Other than the point of the resin composition prepared by mixing a mixture of azatriphosphorus benzene, 5 parts by mass of IRGACURE 184 (manufactured by CIBA SPECIALTY CHEMICALS), 82 parts by mass of 2-butanone, and 18 parts by mass of cyclopentanone The polarizing plate was produced in the same manner.

When the obtained polarizing plate was applied to the flammability test of FMVSS 302, the burning rate was 102 mm/min or less, and it was confirmed that the polarizing plate satisfying the standard was obtained.

[Embodiment 6]

In addition to the TAC film having the FR layer produced in Example 2, 80 parts by mass of pentaerythritol hexaacrylate (KAYARAD PET-30 manufactured by Nippon Kayaku Co., Ltd.) and 20 parts by mass were used as the resin composition. , 2,4,4,6,6-Land [2-(methacryloxy)ethoxy]-1,3,5,2,4,6-triazatriphosphorane, 5 mass A polarizing plate was produced in the same manner as in Example 2 except that a resin composition prepared by mixing IRGACURE 184 (manufactured by CIBA SPECIALTY CHEMICALS), 82 parts by mass of 2-butanone, and 18 parts by mass of cyclopentanone was used.

When the obtained polarizing plate was applied to the flame resistance test of FMVSS 302, the burning rate was 102 mm/min or less, and it was confirmed that a polarizing plate satisfying the standard was obtained.

[Embodiment 7]

In addition to the TAC film having the FR layer produced in Example 2, 25 parts by mass of pentaerythritol hexaacrylate (KAYARAD PET-30 manufactured by Nippon Kayaku Co., Ltd.) and 75 parts by mass were used as the resin composition. , 2,4,4,6,6-Land [2-(methacryloxy)ethoxy]-1,3,5,2,4,6-triazatriphosphorane, 5 mass A polarizing plate was produced in the same manner as in Example 2 except that a resin composition prepared by mixing IRGACURE 184 (manufactured by CIBA SPECIALTY CHEMICALS), 82 parts by mass of 2-butanone, and 18 parts by mass of cyclopentanone was used.

When the obtained polarizing plate was applied to the flammability test of FMVSS 302, the burning rate was 102 mm/min or less, and it was confirmed that the polarizing plate satisfying the standard was obtained.

[Embodiment 8]

In addition to the TAC film having the FR layer produced in Example 2, 60 parts by mass of pentaerythritol hexaacrylate (KAYARAD PET-30 manufactured by Nippon Kayaku Co., Ltd.), 40 parts by mass, was used as the resin composition. , 2,4,4,6,6-lu (phenoxy)-1,3,5,2,4,6-triazatriphosphorane (SPS-100, manufactured by Otsuka Chemical Co., Ltd.), 5 mass A polarizing plate was produced in the same manner except that the resin composition prepared by mixing IRGACURE 184 (manufactured by CIBA SPECIALTY CHEMICALS), 82 parts by mass of 2-butanone, and 18 parts by mass of cyclopentanone was used.

When the obtained polarizing plate was applied to the flame resistance test of FMVSS 302, the burning rate was 102 mm/min or less, and it was confirmed that a polarizing plate satisfying the standard was obtained.

[Embodiment 9]

In addition to the TAC film having the FR layer produced in Example 2, 60 parts by mass of pentaerythritol hexaacrylate (KAYARAD PET-30 manufactured by Nippon Kayaku Co., Ltd.) and 40 parts by mass were used as the resin composition. Examples of the flame retardant compound PP-18 (FRM-1000 manufactured by Nippon Kayaku Co., Ltd.), 5 parts by mass of IRGACURE 184 (manufactured by CIBA SPECIALTY CHEMICALS), 82 parts by mass of 2-butanone, and 18 parts by mass of cyclopentanone A polarizing plate was produced in the same manner except for the point of the resin composition to be prepared.

When the obtained polarizing plate was applied to the flammability test of FMVSS 302, the burning rate was 102 mm/min or less, and it was confirmed that the polarizing plate satisfying the standard was obtained.

[Embodiment 10]

In addition to the TAC film having the FR layer produced in Example 2, 55 parts by mass of pentaerythritol hexaacrylate (KAYARAD PET-30 manufactured by Nippon Kayaku Co., Ltd.) and 45 parts by mass were used as the resin composition. Examples of the flame retardant compound PP-18 (FRM-1000 manufactured by Nippon Kayaku Co., Ltd.), 5 parts by mass of IRGACURE 184 (manufactured by CIBA SPECIALTY CHEMICALS), 82 parts by mass of 2-butanone, and 18 parts by mass of cyclopentanone A polarizing plate was produced in the same manner except for the point of the resin composition to be prepared.

When the obtained polarizing plate was applied to the flammability test of FMVSS 302, the burning rate was 102 mm/min or less, and it was confirmed that the polarizing plate satisfying the standard was obtained.

[Example 11]

In addition to the TAC film having the FR layer produced in Example 2, 70 parts by mass of pentaerythritol hexaacrylate (KAYARAD PET-30 manufactured by Nippon Kayaku Co., Ltd.) and 35 parts by mass of the compound were used as the resin composition. The same applies to the resin composition prepared by mixing PP-1 (manufactured by Sanko Co., Ltd.), 5 parts by mass of IRGACURE 184 (manufactured by CIBA SPECIALTY CHEMICALS), 82 parts by mass of 2-butanone, and 18 parts by mass of cyclopentanone. The polarizing plate is manufactured by performing it.

When the obtained polarizing plate was applied to the flammability test of FMVSS 302, the burning rate was 102 mm/min or less, and it was confirmed that the polarizing plate satisfying the standard was obtained.

[Embodiment 12]

A polarizing plate was produced in the same manner as in Example 1 except that the TAC film having the FR layer was produced in the same manner as in Example 1 except that the film thickness of the FR layer was changed to 2 μm instead of 5 μm.

When the obtained polarizing plate was applied to the flammability test of FMVSS 302, the burning rate was 102 mm/min or less, and it was confirmed that the polarizing plate satisfying the standard was obtained.

[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-dimethyl acrylamide were dissolved in 185 parts by mass of ethyl acetate, and azobisisobutyronitrile was added thereto. The mass fraction was reacted at 70 ° C for 5 hours to obtain an acrylic copolymer resin (weight average molecular weight: 1,3,500,000, Tg: -37 ° C). Next, an acrylic copolymer resin solution (viscosity: 2,000 cps/25 ° C) prepared by using ethyl acetate as a resin content of 20% by mass was used to prepare 100 parts by mass of the resin solid content of the acrylic copolymer resin solution. , toluene diisocyanate (3 mol) of trimethylolpropane (1 mol) adduct 0.5 parts by mass, γ-glycidoxypropyl methoxy decane 0.5 parts by mass, and 9,10-di 30 parts by mass of hydrogen-9-oxa-10-phosphaphenanthrene-10-peroxide (HCA manufactured by Sanko Co., Ltd.) was stirred to obtain an adhesive resin composition. Two sets of the polarizing element obtained in accordance with Example 1 (2) were obtained by laminating two TACs using a 4% by mass aqueous solution of polyvinyl alcohol, and the TAC/polarizing element/TAC was obtained. Two sets of TAC/polarizing element/TAC were bonded by using an adhesive resin composition with an adhesive layer having a thickness of 22 μm therebetween. Next, an adhesive layer having a thickness of 22 μm formed on the release film using the adhesive resin composition was attached to the TAC surface of one of the obtained laminates in the following order: TAC/polarizing element/TAC/containing Adhesive layer of Teflon compound/TAC/polarizing element/TAC/Adhesive layer/release film containing phosphaphenanthrene compound A polarizing plate in which these elements are laminated is produced.

When the obtained polarizing plate was applied to the flammability test of FMVSS 302, it was confirmed that a polarizing plate satisfying the standard was obtained.

[Embodiment 14]

In addition to the use of cyclic phenoxyphosphazene (SPE-100 manufactured by Otsuka Chemical Co., Ltd.) 20 parts by mass in place of 9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-peroxide (Sanguang Co., Ltd.) A polarizing plate was produced in the same manner as in Example 13 except that the HCA was 30 parts by mass.

When the obtained polarizing plate was applied to the flammability test of FMVSS 302, it was confirmed that a polarizing plate satisfying the standard was obtained.

[Example 15]

In addition to the use of a cyclic phenoxyphosphazene (SPE-100 manufactured by Otsuka Chemical Co., Ltd.) 40 parts by mass in place of 9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-peroxide (Sanguang Co., Ltd.) A polarizing plate was produced in the same manner as in Example 13 except that the HCA was 30 parts by mass.

When the obtained polarizing plate was applied to the flammability test of FMVSS 302, it was confirmed that a polarizing plate satisfying the standard was obtained.

[Example 16]

83 parts by mass of n-butyl acrylate, 1 part by mass of 2-hydroxyethyl acrylate, and 12 parts by mass of N,N-dimethyl decylamine, hexa(methyl propylene oxime extended ethyl dioxy) ring three 8 parts by mass of phosphazene (PPZ monomer manufactured by Idemitsu Petrochemical Co., Ltd.) was dissolved in 185 parts by mass of ethyl acetate, and 0.05 parts by mass of azobisisobutyronitrile was added thereto, and reacted at 70 ° C for 5 hours to obtain an acrylic copolymer resin ( Weight average molecular weight: 1,3,500,000, Tg: -37 ° C). In addition, an acrylic copolymer resin solution (viscosity: 2,000 cps/25 ° C) prepared by using ethyl acetate as a resin content of 20% by mass was used to prepare 100 parts by mass of the resin solid content of the acrylic copolymer resin solution. , toluene diisocyanate (3 mol) of trimethylolpropane (1 mol) adduct 0.5 parts by mass, γ-glycidoxypropyl methoxy decane 0.5 parts by mass, and 9,10-di 30 parts by mass of hydrogen-9-oxa-10-phosphaphenanthrene-10-peroxide (HCA manufactured by Sanko Co., Ltd.) was stirred to obtain an adhesive resin composition. Two sets of the polarizing element obtained in accordance with Example 1 (2) were obtained by laminating two TACs using a 4% by mass aqueous solution of polyvinyl alcohol, and the TAC/polarizing element/TAC was obtained. Two sets of TAC/polarizing element/TAC were bonded by using an adhesive resin composition with an adhesive layer having a thickness of 22 μm therebetween. Next, an adhesive layer having a thickness of 22 μm formed on the release film using the adhesive resin composition was attached to the TAC surface of one of the obtained laminates in the following order: TAC/polarizing element/TAC/containing Adhesive layer of phosphazene compound/TAC/polarizing element/TAC/Adhesive layer/release film containing phosphazene compound A polarizing plate in which these elements are laminated is produced.

When the obtained polarizing plate was applied to the flammability test of FMVSS 302, it was confirmed that a polarizing plate satisfying the standard was obtained.

[Example 17]

In addition to the TAC film having the FR layer produced in Example 2, as the resin composition, 95 parts by mass of 2,2,4,4,6,6-land [2-(methacrylic) having flame retardancy was used.醯oxy)ethoxy]-1,3,5,2,4,6-triazatriphosphorane (produced by Idemitsu Petrochemical Co., Ltd., PPZ monomer), 5 parts by mass of IRGACURE 184 (CIBA SPECIALTY CHEMICALS A polarizing plate was produced in the same manner except that the resin composition prepared by mixing 82 parts by mass of 2-butanone and 18 parts by mass of cyclopentanone was used.

When the obtained polarizing plate was applied to the flammability test of FMVSS 302, the burning rate was 102 mm/min or less, and it was confirmed that the polarizing plate satisfying the standard was obtained.

[Comparative Example 1]

In addition to the TAC film having the FR layer produced in Example 1, as the resin composition, 100 parts by mass of pentaerythritol hexaacrylate (KAYARAD PET-30 manufactured by Nippon Kayaku Co., Ltd.) and 5 parts by mass of IRGACURE were used. a resin composition containing no halogen-containing flame retardant prepared by mixing 184 (manufactured by CIBA SPECIALTY CHEMICALS), 82 parts by mass of 2-butanone, and 18 parts by mass of cyclopentanone, and manufactured under the same conditions as those of the FR layer. In the same manner as in the first embodiment, the HC layer/TAC/polarizing element/TAC/HC layer was used to produce a polarizing plate in which these elements were laminated.

When the obtained polarizing plate was applied to the flammability test of FMVSS 302, the burning speed in the extending direction was 127.1 mm/min, and the burning rate was 102 mm/min or less.

[Comparative Example 2]

In addition to the TAC film having the FR layer produced in Example 2, 100 parts by mass of pentaerythritol hexaacrylate (KAYARAD PET-30 manufactured by Nippon Kayaku Co., Ltd.) and 5 parts by mass of IRGACURE were used as the resin composition. a resin composition containing no halogen-containing flame retardant prepared by mixing 184 (manufactured by CIBA SPECIALTY CHEMICALS), 82 parts by mass of 2-butanone, and 18 parts by mass of cyclopentanone, and manufactured under the same conditions as those of the FR layer. The same as in the second embodiment except for the HC layer, in the following order: HC layer/TAC/polarizing element/TAC/adhesive layer/TAC/polarizing element/TAC/HC layer manufacturing layered with these elements Polarizer.

When the obtained polarizing plate was applied to the flame resistance test of FMVSS 302, the burning speed in the extending direction was 123.9 mm/min, and the burning rate was 102 mm/min or less.

[Comparative Example 3]

A polarizing plate was produced in the same manner as in the production of the TAC film having the FR layer in Example 1, except that the film thickness of the FR layer after drying the solvent was 0.09 μm instead of 5 μm.

When the obtained polarizing plate was applied to the flammability test of FMVSS 302, the reference of the burning speed of 102 mm/min or less was not satisfied.

[Comparative Example 4]

The same procedure as in Example 1 was carried out except that a TAC film having no FR layer was used instead of the TAC film having the FR layer, and a polarizing plate in which the elements were laminated in accordance with the following procedure: TAC/polarizing element/TAC .

When the obtained polarizing plate was applied to the flammability test of FMVSS 302, the reference of the burning speed of 102 mm/min or less was not satisfied.

[Comparative Example 5]

Except that the production of the adhesive resin composition does not mix 9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-peroxide (HCA manufactured by Sanguang Co., Ltd.), and examples 13 was carried out in the same manner to manufacture a polarizing plate.

When the obtained polarizing plate was applied to the flammability test of FMVSS 302, the reference of the burning speed of 102 mm/min or less was not satisfied.

From the results of the above Examples 1 to 17 and Comparative Examples 1 to 5, it can be understood that the flame retardant layer of the present invention does not lower the transmittance and the degree of polarization of the polarizing element and has high flame retardancy, and is displayed. A polarizing plate of FMVSS 302 that meets the safety specifications of the United States can be obtained. By applying the polarizing plate with the flame retardant layer of the present invention to the vehicle monitor or the vehicle interior decoration, it has bright and high polarization performance, and also has excellent flame retardancy and can be used for the operator or The same passenger provides security. Further, in recent years, when a project for insurance application is required to have flame retardancy and low flammability, the flame retardant layer of the present invention can continue the liquid crystal display device of various industrial devices and household electrochemical products for a long period of time. Improve durability and reliability.

Claims (10)

 A flame retardant polarizing plate comprising a flame retardant layer having a thickness of 0.1 to 100 μm and a polarizing element, wherein the flame retardant layer contains 5 to 99% by mass of a compound having a phosphophenanthrene skeleton and/or A compound of the phosphazene skeleton.    The flame-retardant polarizing plate according to claim 1, wherein the flame-retardant layer contains: 5 to 80% by mass of a compound having a phosphaphenanthrene skeleton and/or a compound having a phosphazene skeleton, and a cured product of a resin composition different from the compound having a phosphaphenanthene skeleton and/or the compound having a phosphazene skeleton, or a (meth) acrylate compound; or 10 to 99.9% by mass of (meth) A cured product of a resin composition of a propylene fluorenyl group having a phosphaphenanthene skeleton and/or a compound having a phosphazene skeleton having a (meth) acrylonitrile group.    The flame retardant polarizing plate according to claim 1 or 2, wherein the compound having a phosphaphenanthrene skeleton is a compound having a 10-sided oxy-9-oxa-10-phosphaphenanthroline skeleton.   The flame retardant polarizing plate according to claim 3, wherein the compound having a 10-sided oxy-9-oxa-10-phosphaphenanthroline skeleton is a compound represented by the formula (1): In the formula, R ₁ is a (meth) acrylonitrile group or a substituent having a (meth) acryl fluorenyl group.  The flame retardant polarizing plate according to claim 1 or 2, wherein the compound having a phosphazene skeleton has a 1,3,5,2,4,6-triazatriphosphorane skeleton. Compound.   The flame-retardant polarizing plate according to claim 5, wherein the compound having a 1,3,5,2,4,6-triazatriphosphorane skeleton is represented by the formula (2) Compound: In the formula, R ₂ to R ₇ each independently represent a (meth)acryl fluorenyl group or a substituent having a (meth) acrylonitrile group.  The flame retardant polarizing plate according to any one of claims 2 to 6, wherein all or a part of the (meth) acrylate compound has a hydroxyl group and contains 25 to 90 in the resin composition. quality%.    The flame-retardant polarizing plate according to any one of claims 1 to 7, wherein the flame-retardant layer is selected from the group consisting of an adhesive layer, an adhesive layer, a hard coat layer, and a protective layer. Floor.    The flame-retardant polarizing plate according to any one of claims 1 to 8, wherein the flame-retardant layer is provided on an environmental exposure surface side and/or a light source exposure surface side of the polarizing element.    A liquid crystal display device comprising the flame retardant polarizing plate according to any one of claims 1 to 9.