JPWO2014192413A1 - Anti-fogging agent for cyclic olefin-based resin, cyclic olefin-based resin composition containing the anti-fogging agent, and optical material and optical component using the composition - Google Patents

Abstract

To provide a cyclic olefin resin composition in which the transparency and heat resistance of the cyclic olefin resin are not impaired, and an optical material and an optical component using the composition. The present invention is an anti-fogging agent for cyclic olefin resins which is contained in a cyclic olefin resin composition containing a cyclic olefin resin and maintains the transparency and heat resistance of a molded product obtained from the cyclic olefin resin composition. An anti-fogging agent for cyclic olefin resins comprising a condensed phosphate ester is provided.

Description

  The present invention relates to an anti-fogging agent for cyclic olefin resins, a cyclic olefin resin composition containing the anti-fogging agent, and an optical material and an optical component using the composition.

  Cyclic olefin resins are used for optical materials and the like because they are excellent in transparency and heat resistance. On the other hand, since the molded product containing the cyclic olefin-based resin may be fogged on the surface of the molded product when irradiated with visible light in a wet heat environment, the transparency may be impaired.

  For example, in Patent Document 1, 100 parts by weight of a cyclic olefin resin and 2 to 40 parts by weight of a condensed phosphate ester were blended for the purpose of imparting flame retardancy without impairing the transparency of the cyclic olefin resin. A composition is disclosed.

JP 2006-328174 A

  However, in the composition described in Patent Document 1, since the content of the condensed phosphate ester in the composition is high, properties other than the transparency possessed by the cyclic olefin resin, in particular, heat resistance, etc. are impaired, and the heat environment May cause yellowing of the cyclic olefin resin. Moreover, in the composition of patent document 1, since content of the condensed phosphate ester in a composition is high, a condensed phosphate ester cannot fully melt | dissolve in a cyclic olefin resin, but can cause phase separation. Moreover, elution of a phosphorus compound from a molded product or the like occurs particularly under wet heat conditions, and the transparency of a molded product obtained from the composition may be reduced. In addition, since the condensed phosphate ester generally has a smaller molecular weight than the cyclic olefin resin, if an excessive amount of the condensed phosphate ester is present in the composition, the Tg, melt viscosity, and heat resistance of the cyclic olefin resin. There is a possibility that the property, toughness, etc. may be reduced.

  On the other hand, as long as the problem in Patent Document 1 is to impart flame retardancy to the cyclic olefin resin, the content of the condensed phosphate ester cannot be reduced. Therefore, in Patent Document 1, it is difficult to obtain a composition in which the transparency and heat resistance of the cyclic olefin resin are not impaired.

  The present invention has been made in view of the problems as described above, and a cyclic olefin resin composition in which the transparency and heat resistance of the cyclic olefin resin are not impaired, and an optical system using the composition. The object is to provide materials and optical components.

  The present inventors have found that the above-mentioned problems can be solved by the anti-fogging agent for cyclic olefin resin comprising a condensed phosphate ester, and have completed the present invention. More specifically, the present invention provides the following.

  (1) An anti-fogging agent for cyclic olefin resins which is contained in a cyclic olefin resin composition containing a cyclic olefin resin and maintains the transparency and heat resistance of a molded product obtained from the cyclic olefin resin composition. An anti-fogging agent for cyclic olefin resins comprising a condensed phosphate ester.

（一般式（Ｉ）中、Ｒ^１、Ｒ^２、Ｒ^４〜Ｒ^６は、それぞれ独立に、炭素数６〜２０のアリール基を表し、Ｒ^３は炭素数６〜２５のアリーレン基を表し、ｎは０〜３の整数を示す。）(2) The anti-fogging agent for cyclic olefin resin according to (1), wherein the condensed phosphate ester is a compound represented by the following general formula (I).

(In general formula (I), R ¹ , R ² , R ^{4 to} R ⁶ each independently represents an aryl group having 6 to 20 carbon atoms, R ³ represents an arylene group having 6 to 25 carbon atoms, n represents an integer of 0 to 3.)

(3) The anti-fogging agent for cyclic olefin-based resins according to (2), wherein the condensed phosphate ester is a compound represented by the following general formula (II) or (IV).

(4) including a cyclic olefin-based resin and the anti-fogging agent for cyclic olefin-based resin according to any one of (1) to (3),
Content of the said anti-fogging agent for cyclic olefin resin is a cyclic olefin resin composition which is 0.05 mass part or more and 1 mass part or less with respect to 100 mass parts of said cyclic olefin resins.

  (5) At least a master batch containing 100 parts by mass of the cyclic olefin resin and 0.5 to 10 parts by mass of the antifogging agent for cyclic olefin resin according to any one of (1) to (3). The cyclic olefin resin composition according to (4), which is mixed with a cyclic olefin resin.

  (6) An optical material comprising the cyclic olefin-based resin composition according to (4) or (5).

  (7) An optical component formed by molding the cyclic olefin-based resin composition according to (4) or (5).

  (8) The optical component according to (7), wherein the optical component is any one of a light guide plate, a lens, and a lamp cover.

  According to the present invention, there are provided a cyclic olefin resin composition in which the transparency and heat resistance of the cyclic olefin resin are not impaired, and an optical material and an optical component using the composition.

  Hereinafter, embodiments of the present invention will be described in detail. In addition, this invention is not limited to the following embodiment.

[Anti-fogging agent for cyclic olefin resin]
The anti-fogging agent for cyclic olefin resins of the present invention (hereinafter also referred to as “fogging preventive agent of the present invention”) comprises a condensed phosphate ester. In the present specification, “fogging prevention” means that the transparency inherent in the cyclic olefin-based resin is not reduced by the molding process, and the cloudiness inside the molded body due to an environmental change to which the molded body is subsequently exposed. As a result, it refers to preventing the occurrence of “cloudiness” caused by a decrease in the transparency of the molded body.

  Conventionally, condensed phosphate esters have been used as flame retardants for imparting flame retardancy to cyclic olefin resins. However, the anti-fogging agent of the present invention does not have the function of imparting flame retardancy to the cyclic olefin resin, and has the function of maintaining the transparency and heat resistance of the cyclic olefin resin exclusively. A distinction is made between anti-fogging agents and conventional flame retardants containing condensed phosphate esters. Specifically, the use of the condensed phosphate ester as an anti-fogging agent and the use of the condensed phosphate ester as a flame retardant differ in the amount of the condensed phosphate ester used as described later.

(Condensed phosphate ester)
Although the condensed phosphate ester in this invention is not specifically limited, The condensed phosphate ester etc. which have an aromatic ring are mentioned. The phosphorus atom in the condensed phosphate ester is pentavalent, and has less effect on oxidation due to oxidation compared to phosphorus compounds containing trivalent phosphorus atoms, and suppresses discoloration such as yellowing in a thermal environment Is done. Condensed phosphate ester may be used individually by 1 type, or may be used in combination of 2 or more type.

（一般式（Ｉ）中、Ｒ^１、Ｒ^２、Ｒ^４〜Ｒ^６は、それぞれ独立に、炭素数６〜２０のアリール基を表し、Ｒ^３は炭素数６〜２５のアリーレン基を表し、ｎは０〜３の整数を示す。）For example, the structure of the preferable condensed phosphate ester in the present invention includes a compound represented by the following general formula (I).

(In general formula (I), R ¹ , R ² , R ^{4 to} R ⁶ each independently represents an aryl group having 6 to 20 carbon atoms, R ³ represents an arylene group having 6 to 25 carbon atoms, n represents an integer of 0 to 3.)

In the general formula (I), examples of the aryl group represented by R ¹ , R ² , R ^{4 to} R ⁶ include a phenyl group, a naphthyl group, and a biphenylene group. The aryl group may have an alkyl group such as a methyl group or an ethyl group as a substituent. Examples of the arylene group represented by R ³ include a phenylene group, a naphthylene group, a biphenylene group, and a bisphenol residue.

  Known compounds can be used as the compound represented by the general formula (I). For example, 1,3 phenylene bis (diphenyl phosphate), 1,3 phenylene bis (di-4 methylphenyl phosphate), 1,3 phenylene bis (di-2,6 xylenyl phosphate), 1,4 phenylene bis (diphenyl) Phosphate), 1,4 phenylene bis (di-2,6 xylenyl phosphate), 4,4 'biphenylene bis (diphenyl phosphate), 4,4' biphenylene bis (di-2, 6 xylenyl phosphate); these And hydroquinone phosphates, biphenol phosphates and biphenol-A phosphates corresponding to these phosphates. These compounds may be used alone or in combination of two or more.

Among the compounds represented by the general formula (I), the compounds represented by the following general formula (II) (1,3 phenylene bis) are particularly effective in maintaining the transparency and heat resistance of the cyclic olefin resin. (Di-2,6 xylenyl phosphate), also known as resorcinol bis (di-2,6 xylenyl phosphate)), or a compound represented by the following general formula (IV) (4,4′biphenylenebis (di- 2,6 xylenyl phosphate)) is particularly preferred.

(Cyclic olefin resin)
The cyclic olefin resin in the present invention is not particularly limited as long as it is a polymer or copolymer containing a structural unit derived from a cyclic olefin in the main chain. For example, an addition polymer of a cyclic olefin or a hydrogenated product thereof, an addition copolymer of a cyclic olefin and an α-olefin, or a hydrogenated product thereof can be used. A cyclic olefin resin can be used individually by 1 type, or can also use 2 or more types together.

  In addition, examples of the cyclic olefin-based resin include those obtained by grafting and / or copolymerizing an unsaturated compound having a polar group in the polymer or the copolymer containing a structural unit derived from a cyclic olefin in the main chain. It is done.

  Examples of the polar group include a carboxyl group, an acid anhydride group, an epoxy group, an amide group, an ester group, and a hydroxyl group. Examples of the unsaturated compound having a polar group include (meth) acrylic acid and maleic acid. Acid, maleic anhydride, itaconic anhydride, glycidyl (meth) acrylate, alkyl (meth) acrylate (carbon number 1-10) ester, maleic acid alkyl (carbon number 1-10) ester, (meth) acrylamide, (meta ) 2-hydroxyethyl acrylate.

  In addition, a commercially available resin can be used as the copolymer used as the cyclic olefin resin in the present invention. Examples of commercially available cyclic olefin-based resins include TOPAS (registered trademark) (manufactured by TOPAS Advanced Polymers), Apel (registered trademark) (manufactured by Mitsui Chemicals), Zeonex (registered trademark) (manufactured by ZEON Corporation), Examples include ZEONOR (registered trademark) (manufactured by ZEON Corporation), ARTON (registered trademark) (manufactured by JSR Corporation), and the like.

（式中、Ｒ^１〜Ｒ^１２は、それぞれ同一でも異なっていてもよく、水素原子、ハロゲン原子、及び、炭化水素基からなる群より選ばれるものであり、
Ｒ^９とＲ^１０、Ｒ^１１とＲ^１２は、一体化して２価の炭化水素基を形成してもよく、
Ｒ^９又はＲ^１０と、Ｒ^１１又はＲ^１２とは、互いに環を形成していてもよい。
また、ｎは、０又は正の整数を示し、
ｎが２以上の場合には、Ｒ^５〜Ｒ^８は、それぞれの繰り返し単位の中で、それぞれ同一でも異なっていてもよい。）Particularly preferable examples of the addition copolymer of cyclic olefin and α-olefin include [1] a structural unit derived from an α-olefin having 2 to 20 carbon atoms, and [2] represented by the following general formula (III). And a copolymer containing a structural unit derived from a cyclic olefin.

(Wherein R ^{1 to} R ¹² may be the same as or different from each other, and are selected from the group consisting of a hydrogen atom, a halogen atom, and a hydrocarbon group;
R ⁹ and R ¹⁰ , R ¹¹ and R ¹² may be integrated to form a divalent hydrocarbon group,
R ⁹ or R ¹⁰ and R ¹¹ or R ¹² may form a ring with each other.
N represents 0 or a positive integer;
When n is 2 or more, R ^{5 to} R ⁸ may be the same or different in each repeating unit. )

[[1] α-olefin having 2 to 20 carbon atoms]
The α-olefin having 2 to 20 carbon atoms is not particularly limited. For example, the thing similar to Unexamined-Japanese-Patent No. 2007-302722 can be mentioned. These α-olefins may be used alone or in combination of two or more. Of these, ethylene is most preferably used alone.

[[2] Cyclic olefin represented by general formula (III)]
The cyclic olefin represented by the general formula (III) will be described. R ^{1 to} R ¹² in the general formula (III) may be the same or different and are selected from the group consisting of a hydrogen atom, a halogen atom, and a hydrocarbon group. Specific examples of the cyclic olefin represented by the general formula (III) include those similar to those described in JP-A-2007-302722.

  These cyclic olefins may be used singly or in combination of two or more. Among these, it is preferable to use bicyclo [2.2.1] hept-2-ene (common name: norbornene) alone.

  [1] A polymerization method of an α-olefin having 2 to 20 carbon atoms and a cyclic olefin represented by [2] general formula (III) and a hydrogenation method of the obtained polymer are not particularly limited. Can be carried out according to a known method.

  The polymerization catalyst used is not particularly limited, and a cyclic olefin resin can be obtained by a known method using a conventionally known catalyst such as a Ziegler-Natta, metathesis, or metallocene catalyst.

[Cyclic olefin resin composition]
The anti-fogging agent of the present invention is contained in a cyclic olefin resin composition containing a cyclic olefin resin (hereinafter, the cyclic olefin resin composition containing the anti-fogging agent of the present invention is also referred to as “the composition of the present invention”). Is done. Thereby, since the cloudiness of cyclic olefin resin and the heat resistance fall of cyclic olefin resin can be suppressed, the transparency and heat resistance of the molded object obtained from a cyclic olefin resin composition are maintained.

  In the present invention, “maintaining the transparency of the molded product obtained from the cyclic olefin-based resin composition” means that the molded product obtained from the composition of the present invention is subjected to a visible light irradiation test in the wet heat environment shown in the examples. In the case of performing the test, it means that the molded product is hardly fogged by visual observation even after the test.

  In the present invention, “maintaining the heat resistance of the molded product obtained from the cyclic olefin-based resin composition” means that the molded product obtained from the composition of the present invention has a heat resistance under a temperature condition close to the Tg of the cyclic olefin-based resin. When the property test (110 ° C., 1000 hours) is performed, a value obtained by subtracting the yellowness of the molded product before the heat resistance test from the yellowness (DIN6167) of the molded product after the heat resistance test (also referred to as “ΔYI”). ) Is less than 1. That ΔYI is less than 1 indicates that yellowing of the molded body is substantially suppressed even in a thermal environment.

  The amount of the anti-fogging agent of the present invention contained in the composition of the present invention is 0.05 parts by mass or more and 1 part by mass or less with respect to 100 parts by mass of the cyclic olefin resin. When the amount of the anti-fogging agent of the present invention is 0.05 parts by mass or more, preferably 0.08 parts by mass or more, more preferably 0.1 parts by mass or more, relative to 100 parts by mass of the cyclic olefin resin. The fogging of the olefin resin can be prevented and the transparency is not easily lost. When the amount of the anti-fogging agent of the present invention is 1 part by mass or less, preferably 0.8 parts by mass or less, more preferably 0.5 parts by mass or less, with respect to 100 parts by mass of the cyclic olefin resin. The transparency and heat resistance of the resin are not easily impaired.

  When the anti-fogging agent of the present invention is more than 1 part by mass (for example, 2 parts by mass or more) with respect to 100 parts by mass of the cyclic olefin resin, flame retardant properties can be imparted to the cyclic olefin resin. The heat resistance of the resin is impaired and the effect of the anti-fogging agent of the present invention is not achieved. Furthermore, when the blending amount is such, the condensed phosphate ester does not sufficiently dissolve in the cyclic olefin resin, causing phase separation, and elution of the phosphorus compound from the molded product occurs particularly under wet heat conditions. The transparency of the molded product obtained from the composition may be reduced. Moreover, the polymer characteristics (Tg, melt viscosity, heat resistance, toughness, etc.) of the cyclic olefin resin can be reduced.

  In the composition of the present invention, further known additives (antioxidants, hindered amine light stabilizers, ultraviolet light absorbers, flame retardants, sulfur stabilizers, metal extractants, as long as the object of the present invention is not impaired) Etc.) may be added. The kind and amount of the additive in the cyclic olefin-based resin composition can be appropriately adjusted according to the effect to be obtained.

(Method for producing cyclic olefin-based resin composition)
The manufacturing method of the cyclic olefin resin composition of this invention is not specifically limited, A well-known method is employable. Examples thereof include a method of melt-kneading the cyclic olefin resin, the anti-fogging agent for the cyclic olefin resin, or a resin blended as necessary, all at once or sequentially. Examples of the melt-kneading method include a method of blending the resin composition and then melt-kneading with a uniaxial or biaxial screw extruder, a Banbury mixer, a roll, various kneaders, and the like. The temperature in the melt kneading is not particularly limited as long as the cyclic olefin resin, the cyclic olefin resin anti-fogging agent, and the resin blended as necessary are melted, but usually 160 ° C to 350 ° C, preferably Is generally carried out in a temperature range of 180 ° C to 300 ° C.

  For example, you may prepare the composition of this invention by mixing the component which comprises the composition of this invention at once. Or you may mix the masterbatch containing cyclic olefin resin and the fog prevention agent of this invention with base resin containing cyclic olefin resin etc., and may prepare the composition of this invention. When the composition of the present invention is prepared using a masterbatch, it is preferable in that a composition having high heat resistance and more suppressed yellowing can be obtained.

  The masterbatch that can be used in the present invention is not particularly limited as long as it contains an anti-fogging agent having a higher concentration than the anti-fogging agent in the cyclic olefin-based resin composition to be finally obtained. The master batch that can be used in the present invention includes, for example, 100 parts by mass of a cyclic olefin-based resin and 0.5 to 10 parts by mass of the anti-fogging agent of the present invention.

[Optical materials and optical components]
Since the transparency and heat resistance which cyclic olefin resin has are not impaired, the cyclic olefin resin composition of this invention can be used conveniently as an optical material. Moreover, the optical component excellent in transparency and heat resistance is obtained by shape | molding the composition of this invention and the optical material of this invention. Examples of the optical component include a light guide plate, a lens, and a lamp cover.

  EXAMPLES Hereinafter, although an Example is shown and this invention is demonstrated concretely, this invention is not limited to these Examples.

  The product name: TOPAS (registered trademark) 5013L-10 (manufactured by TOPAS Advanced Polymers, melt viscosity 56 Pa · s, Tg 134 ° C.) was used as the cyclic olefin-based resin. Cyclic olefin resin and various phosphorus compounds are used in the ratios shown in Table 1, and these are melted at a cylinder temperature of 260 ° C. using a twin screw extruder (manufactured by Nippon Steel Works, trade name: TEX30). It knead | mixed and pelletized and obtained the cyclic olefin resin composition of the Example and the comparative example. In Comparative Example 1, only the cyclic olefin resin was melt-extruded with a twin screw extruder. In Comparative Example 9, a cyclic olefin resin not melt kneaded was injection molded.

  Next, using the obtained pellets, a flat plate of 70 mm × 70 mm × 2 mm on an injection molding machine (trade name: SE75D, manufactured by Sumitomo Heavy Industries, Ltd.) at a cylinder temperature of 270 ° C. and a mold temperature of 115 ° C. A test piece was obtained by molding and subjected to the following test.

  The melt viscosity of the cyclic olefin resin was measured at 260 ° C. and a shear rate of 1216 / sec in accordance with ISO11443. Further, the glass transition point (Tg) of the cyclic olefin-based resin was measured by a DSC method (method described in JIS K7121) at a temperature rising rate of 10 ° C./min.

  In Table 1, “total amount compound” means TOPAS5013L-10 as a cyclic olefin-based resin and the components described in Table 1 by melt-kneading with a twin-screw extruder, pelletizing, and then injection molding. The test piece is molded. In addition, “masterbatch” is a masterbatch prepared from a cyclic olefin-based resin and the components described in Table 1, and the masterbatch is adjusted so that the phosphorus concentration becomes the addition amount described in Table 1. The test piece was molded after being diluted with a cyclic olefin resin by pellet blending. As shown in Table 1, the master batch used in the “master batch” is a cyclic olefin resin and various phosphorus compounds in a range of 2 to 8 parts by mass with respect to 100 parts by mass of the cyclic olefin resin. And including. The “valence of phosphorus” refers to the valence of phosphorus atoms in various phosphorus compounds. The “phosphorus addition amount relative to the cyclic olefin resin” refers to the addition amounts of various phosphorus compounds relative to the total cyclic olefin resin used.

The details of each component used in Table 1 are as follows.
PX-200 (corresponding to condensed phosphate ester): 1,3 phenylene bis (di-2,6 xylenyl phosphate), 4,4 ′ biphenylene bis (di-2,6 xyle) manufactured by Daihachi Chemical Industry Co., Ltd. Nyl phosphate) (corresponding to condensed phosphate ester): “Condensed phosphate ester 2” in Table 1
Tridecyl phosphite: HOSTANOX P-EPQ ("P-EPQ" in Table 1) manufactured by Wako Pure Chemical Industries, Ltd .: tetrakis (2,4-di-tert-butylphenyl) -4,4'-biphenylenediphospho Knight, Clariant Japan, Inc. IRGAFOS (registered trademark) 168: Tris (2,4-di-t-butylphenyl) phosphite, BASF Corporation SUMILIZER (registered trademark) GP: 2,4,8,10-tetra-t -Butyl-6- [3- (3-methyl-4-hydroxy-5-t-butylphenyl) propoxy] dibenzo [d, f] [1,3,2] dioxaphosphepine, manufactured by Sumitomo Chemical Co., Ltd. PX-200 / Tinvin 770DF: PX-200 and Tinuvin 770DF (bis (2,2,6,6-tetramethyl-4-pipe) Jiniru) Sebakeito, a blend mixture of Ciba Specialty Chemicals (UK) Limited, Inc.).
TOPAS (registered trademark) 5013L-10 (“5013L-10” in Table 1): Cyclic olefin resin that is a copolymer of norbornene and ethylene, manufactured by TOPAS Advanced Polymers, melt viscosity 56 Pa · s, Tg 134 ° C.

[LED test (visible light irradiation test under humid heat environment)]
About each test piece, the location from the terminal part of a non-gate side to 40 mm was cut out, and the test piece for LED test of 40 mm x 70 mm x 2 mm was obtained. A guide plate having an LED (light beam 20 lm) was attached to the central portion of the terminal portion on the opposite gate side (70 mm from the gate side). Next, each LED test specimen was directly irradiated with light using an LED as a light source, and exposed to a thermo-hygrostat at 60 ° C. × 90% humidity for 1 week, and then the LED was turned off, and then 70 After removing the water vapor in the thermostat at 0 ° C., the test piece for LED test was collected. Each LED test specimen after the LED test was irradiated with light using a halogen bulb (12V100W HAL-L, manufactured by OLYMPUS) as a light source, and the cloudiness of each test specimen was visually observed, and judged according to the following criteria. . The result is shown in the section of “Determination of fogging after LED irradiation” in Table 2.
(Criteria)
◯: No fogging occurred on the test piece by LED irradiation.
X: Clouding occurred in the test piece by LED irradiation.

[Yellowness (YI value)]
About each test piece, the heat resistance test (110 degreeC, 1000 hours) was done. The yellowness (DIN 6167) of each test piece before and after the heat resistance test was measured using a color difference meter color-sphere manufactured by YKB-Gardnar GmbH. The results are shown in the section of “YI value after heat resistance test” in Table 2. In Table 2, “initial YI” indicates the yellowness of each test piece before the heat resistance test. “ΔYI” refers to a value obtained by subtracting the yellowness of each test piece before the heat resistance test from the yellowness of each test piece after the heat resistance test.

  As shown in Table 2, it can be seen that the test piece containing the anti-fogging agent of the present invention is excellent in transparency since fogging is suppressed even after the LED test. Furthermore, it can be seen that the test piece containing the anti-fogging agent of the present invention has a low ΔYI and is excellent in heat resistance because yellowing after the heat resistance test is suppressed. In particular, it can be seen that when a master batch is used, yellowing can be preferably suppressed.

  In addition, the test piece in Comparative Example 9 was fogged, but in other test examples in which melt kneading was performed, no fog was observed. Therefore, the fog was generated due to damage to the resin by melt kneading. You can see that it was not.

Claims (8)

  An anti-fogging agent for cyclic olefin resins, which is contained in a cyclic olefin resin composition containing a cyclic olefin resin and maintains the transparency and heat resistance of a molded product obtained from the cyclic olefin resin composition. An anti-fogging agent for cyclic olefin resins comprising a phosphate ester. The antifogging agent for cyclic olefin-based resins according to claim 1, wherein the condensed phosphate ester is a compound represented by the following general formula (I).

(In general formula (I), R ¹ , R ² , R ^{4 to} R ⁶ each independently represents an aryl group having 6 to 20 carbon atoms, R ³ represents an arylene group having 6 to 25 carbon atoms, n represents an integer of 0 to 3.) The anti-fogging agent for cyclic olefin-based resins according to claim 2, wherein the condensed phosphate ester is a compound represented by the following general formula (II) or (IV).

A cyclic olefin resin, and the anti-fogging agent for cyclic olefin resin according to any one of claims 1 to 3,
Content of the said anti-fogging agent for cyclic olefin resin is a cyclic olefin resin composition which is 0.05 mass part or more and 1 mass part or less with respect to 100 mass parts of said cyclic olefin resins.   A master batch containing 100 parts by mass of the cyclic olefin resin and 0.5 to 10 parts by mass of the anti-fogging agent for cyclic olefin resin according to any one of claims 1 to 3 is at least the cyclic olefin type. The cyclic olefin resin composition according to claim 4, which is mixed with a resin.   An optical material comprising the cyclic olefin-based resin composition according to claim 4.   An optical component formed by molding the cyclic olefin-based resin composition according to claim 4 or 5.   The optical component according to claim 7, wherein the optical component is any one of a light guide plate, a lens, and a lamp cover.