JP3105006B2 - Stabilized polyoxymethylene resin composition - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a polyoxymethylene resin having excellent heat stability and a composition thereof.

[0002]

2. Description of the Related Art Polyoxymethylene resins are well-balanced in various physical properties and are easy to process, so that they can be used as typical engineering plastics, such as electric / electronic parts, automobile parts, etc. It is widely used as a mechanical component. However, with the expansion and diversification of applications, the demand for the quality thereof has been increasing. Required characteristics include a decrease in mechanical strength due to the extrusion or molding process, and adhesion to molds (mold deposit).
Generation, under long-term heating conditions (heat aging)
Reduction of mechanical properties, suppression of coloring of molded articles and the like to a low level can be mentioned. One of the important factors of these phenomena is decomposition of the polymer upon heating.

[0003] Due to its chemical structure, polyoxymethylene inherently has the property of being easily decomposed under acidic or alkaline conditions in a heated oxidizing atmosphere.
To stabilize the chemically active terminal, the terminal of the polymer is esterified by acetylation or the like (homopolymer), or trioxane and a cyclic ether are used during polymerization.
There is a method in which a monomer having an adjacent carbon bond such as cyclic formal is copolymerized, and then the unstable terminal portion is decomposed and removed to make an inactive stable terminal (copolymer). However, upon heating, a cleavage decomposition reaction also occurs in the main chain portion of the polymer, and its prevention cannot be dealt with only by the above treatment, and the addition of antioxidants and other stabilizers is practically essential. I have.

[0004] However, the polyoxymethylene composition containing these stabilizers does not completely suppress the decomposition of the polymer. In practice, during the molding, the action of heat or oxygen in the cylinder of the molding machine is not achieved. Receiving, by main chain decomposition,
Alternatively, formaldehyde is generated from the terminal that is not sufficiently stabilized, and when the working environment is deteriorated during extrusion molding or when molding is performed for a long time, fine powder or tar is attached to the mold surface (mold deposit). ),
It is one of the biggest factors that lowers the working efficiency and deteriorates the surface condition of the molded product. The decomposition of the polymer causes a decrease in mechanical strength and coloring of the resin. Further, when the molded article is heated for a long time (heat aging), the decomposition of the main chain also causes a decrease in mechanical strength and coloring. Under these circumstances, efforts are being made to find more effective stabilizer formulations.

As an antioxidant to be added to the polyoxymethylene resin, a phenol compound having a sterically hindered group (hindered phenol) or an amine compound having a sterically hindered group (hindered amine) is used. Compounds such as polyamides, urea derivatives, amidine compounds, hydroxides of alkali or alkaline earth metals, and organic or inorganic acid salts are used in combination.

[0006] Hindered phenols are particularly effective as antioxidants, while phenols are weak acids,
In addition, since it becomes a strong acid by absorbing light, it can be used as a catalyst for decomposing the polymer as the amount of addition increases. The oxidized form is also likely to be a coloring factor. In some cases, the resin itself causes a mold deposit during molding. Therefore, at the time of molding, heat aging, or under light irradiation conditions, it functions as a stabilizer and at the same time, it is also a factor of polymer decomposition, and the formulation of the stabilizer that balances molding stability, heat aging stability, and weather resistance is delicate. In spite of various proposals and ideas, satisfactory results have not always been obtained.

An object of the present invention is to improve the stability of such polyoxymethylene.

[0008]

Means for Solving the Problems The present inventors have solved the above-mentioned problems and conducted a search for a more effective stabilizer for polyoxymethylene, and as a result, have found that a phenoxy unit is contained in the structure. The present inventors have found that a specific series of compounds including these compounds have an effect as a stabilizer for polyoxymethylene, which led to the present invention.

That is, the present invention relates to a polyoxymethylene resin composition characterized by adding and mixing 0.01 to 5% by weight of a phenoxy compound represented by the general formula (I) with respect to a polyoxymethylene resin. It is intended to improve problems based on stability, such as deterioration of resin due to oxidation or thermal decomposition at the time, generation of mold deposit, deterioration during heat aging, and the like.

[0010] ^{Y 1 -O-Ar 1 -X-} Ar 2 -OY 2 (I) the general formula (I), X is _{-C p H 2p -, -C m} H 2m OC n H 2n -
_{, -C m H 2m SC n H} 2n -, -C p H 2p N (C r H 2r + 1) C q H 2q -, - C p H 2p COC q H 2q -, - C p H 2p COOC
_q H _2q- , -C _p H _2p CON (C _r H _{2r + 1} ) C _q H _2q- , -C _p H _2p S (= O) ₂ C _q H _2q- , -C _p H _2P P (= O) (R) C _q H _2q- , -C _p H _2p P (= O) (R) OC _q H _2q- , -C _p H _2p OP (= O) (R) OC _q H _2q- And m, n are integers from 1 to 20, p, q, r are integers from 0 to 20,
R represents one or more divalent atomic groups selected from C _{1 to} C ₂₀ alkyl, alkoxy groups, or phenyl groups;
That is, they may be used alone or in combination of two or more. Particularly preferably _{-C p H 2p -, -C m} H 2m OC n H 2n -, -C m H 2m SC n H 2n -, -C p H 2p N (C r H 2r + 1) C q H 2q -, C _p H _2p COC _q H _2q- , -C _p H _2p COOC
_q H _2q- , -C _p H _2p S (= O) ₂ C _q H _2q- (However, m, n is an integer of 1-20, p, q, r is an integer of 0-20)
Is a divalent atomic group selected from

-OY ¹ and -OY ² are substituents other than a hydroxyl group, that is, as Y ¹ and Y ² , -C _m H _{2m + 1} ,-(C _m H _2m O) _n C _l H _{2l + 1} , -C _m H _2m SC _p H _{2p + 1} , -C _m H _2m N (C _p H
_{2p + 1} ) (C _q H _{2q + 1} ), -C _m H _2m COC _n H _{2n + 1} , -C _m H _2m COOC _n H _{2n + 1} , -C _m H _2m OCOC _n H
_{2n + 1} , -C _m H _2m CON (C _p H _{2p + 1} ) (C _q H _{2q + 1} ), -C _m H _2m N (C _p H _{2p + 1} ) COC _q H
_{2q + 1} , -C _m H _2m S (= O) ₂ C _n H _{2n + 1} , -C _m H _2m P (= O) (R) C _n H _{2n + 1} , -C _m H
_2m P (= O) (R) OC _n H _{2n + 1} , -C _m H _2m OP (= O) (R) C _n H _{2n + 1} , -C _m H _2m OP (= O) (R) OC _n H _{2n + 1} (where m, n, l are integers from 1 to 20, p, q are integers from 0 to 20,
R is shown an alkyl group of C ₁ -C _20, alkoxy group)
Represents a monovalent group, and among these, -C _m H _{2m + 1 and-} (C _m H _{2m
O) n C l H 2l +} 1 such as an alkyl group or an ether group, preferably, for example, a straight-chain alkyl group as an alkyl group, an isopropyl group, an isobutyl group, sec- butyl group, etc. tert- butyl group, a ether group Ethyl ether group, professional
Pill ether group, butyl ether group, methyl-propyl
Ether group, pentyl ether group, dimethyl-propyl
Examples include an ether group . And -C _m H _2m COOC _n H
_{2n + 1} , -C _m H _2m OCOC _n H _{2n + 1} or -C _m H _2m N (C _p H _{2p + 1} ) (C
_The alkyl ester and alkylamine represented by _{qH 2q + 1} ) are also preferable as Y ¹ and Y ² .

In the general formula (I), Ar ¹ and Ar ² each represent a divalent arylene group such as a phenylene group or a naphthylene group, and a phenylene group is particularly preferable, and -X- and -OY ¹ , -OY ²
May have no substituents other than these, or as other substituents -C _m H _{2m + 1} ,-(C _m H _2m O) _n C _l H _{2l + 1} , -C
_m H _2m SC _p H _{2p + 1} , -C _m H _2m COC _n H _{2n + 1} , -C _m H _2m COOC _n H _{2n + 1} , -C _m H _2m OCOC _n H _{2n + 1} , -C _m H _2m S (= O) ₂
C _n H _{2n + 1} , -C _m H _2m P (= O) (R) C _n H _{2n + 1} , -C _m H _2m P (= O) (R) OC _n H _{2n + 1} , -C _m H _2m OP (= O) (R) C _n H _{2n + 1} , -C _m H _2m OP (= O) (R) OC
_n H _{2n + 1} , -C _m H _2m N (C _p H _{2p + 1} ) (C _q H _{2q + 1} ), -C _m H _2m CON (C _p H _{2p + 1} ) (C _q H
_{2q + 1), -C m H} 2m N (C p H 2p + 1) COC q H 2q + 1 (m, n, l is an integer of 1 to 20, p, q is 0 to 20 integer, R represents C ₁
Alkyl Le group -C _20, or a phenyl group), and may be obtained by introducing selected substituents from phenyl, -C _m H _{2m + 1} as among others an unsubstituted or substituted group, - (C _m H _2m O) _n C _l H
_{2l + 1} , -C _m H _2m COOC _n H _{2n + 1} , -C _m H _2m N (C _p H _{2p + 1} ) (C
_q H _{2q + 1} ) are preferably used. When the compound has such a substituent, it is effective in increasing the reactivity of the present compound or improving the compatibility with the polyoxymethylene resin. The number of these substituents is not limited to one, and a plurality or two or more kinds may be introduced. The substitution position may be any of o-, m- and p-. However, those in which an —OH group is directly bonded to an arylene group (Ar ¹ , Ar ² ) are (I)
Excluded from formula compounds.

The compound of formula (I) is added in an amount of 0.01 to 5% by weight, preferably 0.1 to 2% by weight, based on the polyoxymethylene resin. When the amount of these compounds is too small, the stabilizing effect is poor. On the other hand, when the amount is excessive, the decomposition and discoloration of the polymer may be accelerated, which is not preferable.

A polyoxymethylene compound containing these additives is a high molecular compound having an oxymethylene group as a main structural unit and containing a small amount of a polyoxymethylene homopolymer or a small amount of other structural units in addition to the oxymethylene group. Any of the following copolymers, terpolymers and block copolymers may be used, and the molecules may have not only a linear but also a branched or crosslinked structure. The degree of polymerization is not particularly limited, and any degree may be employed as long as molding is possible.

Although the above compounds have a remarkable stabilizing effect when used alone, they further include nitrogen-containing compounds such as amines and amides, hydroxides of inorganic or alkaline earth metals, inorganic acid salts, carboxylic acid salts, and the like. It is also possible to use one or more metal-containing compounds such as alkoxides and sterically hindered phenol compounds in combination.

Here, the nitrogen-containing compound is nylon 12,
Polyamides such as Nylon 6.12, Nylon 6.66.610, homo- or copolymerized polyamides, substituted polyamides having a methylol group, etc., nylon salts, polyesters such as polyesteramides synthesized from a combination with caprolactam, polyaminotriazole, dicarboxylic acid Acid dihydrazide, heat condensate synthesized by heating from urea, uracils, cyanoguanidines, dicyandiamide, guanamine (2,4-diamino-sym-triazine), melamine, N-butylmelamine, N-phenylmelamine;
N, N-diphenylmelamine, N, N-diallylmelamine, N, N ′, N ″ -triphenylmelamine, N, N
N ', N "-trimethylolmelamine, benzoguanamine, 2,4-diamino-6-methyl-sym-triazine, 2,4-diamino-6-butyl-sym-triazine, 2,4-diamino-6-benzyloxy -Sym-triazine, 2,4-diamino-6-butoxy-sym-triazine, 2,4-diamino-6-cyclohexyl-sy
m-triazine, 2,4-diamino-6-chloro-sym
-Triazine, 2,4-diamino-6-mercapto-sy
m-triazine, 2,4-dioxy-6-amino-sym
-Triazine (Ameride), 2-oxy-4,6-diamino-sym -Triazine (Ameline), N, N,
N ', N'-tetracyanoethylbenzoguanamine and the like. Further, hindered amines described below are also included.

Examples of the metal compound include hydroxides such as sodium, potassium, magnesium, calcium and barium, carbonates, phosphates, silicates, borates, and the like.
Carboxylates such as oxalates, malonates, succinates, adipates, etc., and higher (C ₁₀
-C ₃₂₎ such as salts of substituted higher fatty acids having a substituent such as fatty acid salts and hydroxyl group can be mentioned. Further, basic compounds containing at least one tertiary nitrogen atom and a metal of a carboxylic acid in the same molecule, for example, sodium N-methyliminodiacetate, trisodium nitrilotriacetate, tetrasodium ethylenediaminetetraacetate, dicalcium ethylenediaminetetraacetate, Examples include pentasodium diethylenetriaminepentaacetate, pentapotassium diethylenepentaacetate, pentasodium triethylenetetramine hexaacetate, and sodium ethyleneoxybis (ethylamine) -N, N, N ', N'-4 acetate.

When the compound of the formula (I) in the present invention is used in combination with a known antioxidant, such as a hindered phenol or a hindered amine, the compound has a remarkable synergy in further improving heat stability, especially heat aging characteristics. The effect is recognized.

Examples of the hindered phenol-based antioxidant used for this purpose include, for example, 2,2'-methylenebis (4-methyl-6-tert-butylphenol),
1,6-hexanediol-bis [3- (3,5-di-
tert-butyl-4-hydroxyphenyl) propionate], pentaerythritol tetrakis [3- (3,5
-Di-tert-butyl-4-hydroxyphenyl) propionate], triethylene glycol-bis [3- (3
-Tert-butyl-5-methyl-4-hydroxyphenyl) propionate], N, N'-hexamethylenebis (3,5-di-tert-butyl-4-hydroxy-hydrocinnamide) and the like.

The hindered amine compounds are piperidine derivatives having a sterically hindered group. Examples thereof include 4-acetoxy-2,2,6,6-tetramethylpiperidine and 4-stearoyloxy-2,2. , 6,6-
Tetramethylpiperidine, 4-acryloyloxy-
2,2,6,6-tetramethylpiperidine, 4-methoxy-2,2,6,6-tetramethylpiperidine, 4-benzoyloxy-2,2,6,6-tetramethylpiperidine, 4-cyclohexyloxy- 2,2,6,6-tetramethylpiperidine, 4-phenoxy-2,2,6
6-tetramethylpiperidine, 4-benzyloxy-
2,2,6,6-tetramethylpiperidine, 4- (phenylcarbamoyloxy) -2,2,6,6-tetramethylpiperidine, bis (2,2,6,6-tetramethyl-4-piperidyl) oxalate , Screws (2, 2, 6,
6-tetramethyl-4-piperidyl) malonate, bis (2,2,6,6-tetramethyl-4-piperidyl) adipate, bis (2,2,6,6-tetramethyl-4-)
Piperidyl) sebacate and the like. Also, a high-molecular-weight piperidine derivative polycondensate, for example, dimethyl succinate-1
-(2-hydroxyethyl) -4-hydroxy-2,
2,6,6-tetramethylpiperidine polycondensate is also effective.

The composition of the present invention contains
Or to impart properties according to the purpose to the molded product, general additives to thermoplastic resins, for example, coloring agents such as dyes and pigments, lubricants, nucleating agents, release agents, antistatic agents and other surfactants, Alternatively, one or more kinds of organic polymer materials, inorganic or organic fibrous, powdery, and plate-like fillers can be added.

The method for preparing the composition of the present invention is not particularly limited, and for example, it is effective to simply blend well.
After mixing the respective components, the mixture may be melt-kneaded and extruded by an extruder or the like to form pellets, which may be formed. A method of once preparing pellets having different compositions, mixing the pellets in a predetermined amount, subjecting the mixture to molding, and obtaining a molded article having a desired composition after molding, or a method of directly charging one or more of each component to a molding machine, Either can be used. Further, it is an effective method to make a part of the resin component into a fine powder and to mix and add the other components in order to make the compounding of the additive uniform.

The resin composition according to the present invention can be molded by any of extrusion molding, injection molding, compression molding, vacuum molding, blow molding, foam molding and the like.

[0024]

As shown in the above description and Examples, the compound of formula (I) according to the present invention does not itself contain an element as an acid and hardly becomes a coloring substance. The resin composition has a great effect on suppressing polymer decomposition during molding, preventing the generation of decomposition gas, suppressing the decrease in the degree of polymerization and the accompanying decrease in mechanical strength, and suppressing the occurrence of mold deposits and preventing coloring. In addition, the present invention provides a polyoxymethylene resin or a composition thereof, which is effective for preventing mechanical strength reduction and coloring during heat aging, improving weather resistance, and the like, and having balanced thermal stability. Things.

[0025]

EXAMPLES In order to specifically demonstrate the effects of the present invention,
The present invention will be described with reference to examples, but the present invention is not limited to these examples.

Examples 1 to 5 and Comparative Examples 1 to 2 As Examples 1 to 5 , 100 parts of a polyoxymethylene copolymer resin containing no stabilizer were taken and pulverized, and the following (A) to (E) A compound of

[0027]

Embedded image

0.3 parts by weight of each was added and mixed well under a nitrogen atmosphere. In order to evaluate the degree of polymer main chain decomposition based on the change over time in the melt viscosity accompanying a decrease in molecular weight, 10 g of this mixture was charged into a Takara Kogyo MX101 type melt indexer and melted and retained at 210 ° C for a predetermined time. , Inner diameter 2.09
The weight (MI value) of the resin flowing out per 10 minutes was measured through a mm orifice while applying a load of 2.16 kg.
The measurement was performed after the resin was charged for 7 minutes, 30 minutes, and 60 minutes, and the increase in MI value after 60 minutes, ΔMI = MI (60
Min) -MI (7 minutes). For comparison, a polyoxymethylene copolymer resin without any additives,
And pentaerythrityl-tetrakis [3- (3,5) as a known representative hindered phenolic antioxidant
-Di-tert-butyl-4-hydroxyphenyl) propionate] (Irganox 1010, Ciba-Geigy) 0.3 parts by weight of polyoxymethylene copolymer resin 1
The same measurement was performed for those added to 00 parts by weight (Comparative Examples 1 and 2, respectively). Table 1 shows the results.

[0029]

[Table 1]

By adding the phenoxy compound, the initial MI
Some values increased, but this was thought to be due to the lubricating effect of the additive, and due to a different mechanism from the decomposition of the polymer. The increase of the MI value of the composition of the present invention after 30 minutes is small, and the decomposition of the polymer chain is extremely efficiently suppressed. Further, even after 60 minutes, the increase (ΔMI) is extremely small.

Examples 6 to 10 , Comparative Examples 3 and 4 Polyoxymethylene copolymer resin and additives (A) to (E) were blended according to the same formulation as in Examples 1 to 5 ,
The mixture was melt-kneaded and extruded at 00 ° C. using an extruder to form pellets. Put 8g of these pellets in the melt indexer,
After being melted and retained at 200 ° C for 5 minutes, the mixture is discharged under a load, the formaldehyde generated is collected, measured by the acetylacetone method, and expressed as the weight (ppm) of formaldehyde generated relative to the resin per unit weight. did. For comparison, no additive was added (Comparative Example 3), and
Irganox 1010 was similarly blended (Comparative Example 4). In addition, using these pellets, let them stay in the injection molding machine at a temperature of 200 ° C for 1 hour, and then
A plate-shaped molded product of × 70 mm × 2 mm was molded, and the coloring accompanying the melt retention was measured with a color difference meter Z-1001DP manufactured by Nippon Denshoku Industries Co., Ltd., and the yellowness (JIS K7103) was measured. Furthermore, these pellets were injection-molded at a cylinder temperature of 200 ° C.
70mm x 2mm plate-shaped product and JIS K7113 No. 1 type (thickness 3m
m) A tensile test piece was prepared. This molded product is 8
After standing (heat aging) for days, the retention of the tensile elongation was measured using a tensile test piece, and the coloring (displayed as yellowness) was measured using a plate-like molded product. Table 2 also shows these results.

[0032]

[Table 2]

The compositions (Examples) of the present invention significantly reduce the amount of formaldehyde generated, remarkably reduce coloration during melt retention, improve elongation retention after heat aging, and are also effective in preventing coloration. Was seen.

Examples 11 to 13 and Comparative Examples 5 to 6 Each of the compound (A) was added in an amount of 0.1 and 0.1 parts by weight to 100 parts by weight of a polyoxymethylene copolymer resin containing no additive.
The same evaluation as in Examples 1 to 10 was performed by adding 1,2 parts by weight. For comparison, each additive 0.005, and 10
In the same manner, the addition of 100 parts by weight of the polyoxymethylene copolymer resin was evaluated. Table 3 shows the results.

[0035]

[Table 3]

Although those having an addition amount within the range of the present invention provided favorable results, the addition of 0.005 parts by weight had little effect on polymer decomposition, gas generation and elongation retention, while
Addition of 10 parts by weight resulted in large coloring.

Examples 14 to 18 and Comparative Example 7 Compounds (A) to (A) shown in Examples 1 to 5 were added to 100 parts by weight of a polyoxymethylene copolymer resin containing no additive.
(E) was added in an amount of 0.3 part by weight and melamine in an amount of 0.2 part by weight, and evaluated in the same manner as in Examples 1 to 10 . As a comparative example, the same evaluation was performed when only 0.2 part by weight of melamine was similarly added. The results are shown in Table 4.

[0038]

[Table 4]

In this case, the composition of the present invention was further improved in terms of suppressing the generation of formaldehyde gas and maintaining the elongation after heat aging.

Examples 19 to 22 , Comparative Examples 8 to 9 Of the compounds shown in Examples 1 to 5 , each of (A) and (B)
0.2 parts by weight, and Irga, a phenolic antioxidant
nox 1010 or bis (2,2,6,6-tetramethyl-4-piperidyl) sebacate (Sanol LS-770, manufactured by Sankyo Co., Ltd.) which is a hindered amine antioxidant 0.2
Parts, further added 0.2 part by weight of melamine to 100 parts by weight of a polyoxymethylene copolymer resins, Example 1-10
The same evaluation was performed. As a comparative example, Irganox 10
10 0.4 parts by weight and melamine 0.2 parts by weight (Comparative Example 8),
Alternatively, 0.4 parts by weight of Sanol LS-770 and 0.2 parts by weight of melamine (Comparative Example 9) were added and evaluated in the same manner as in Examples. The results are summarized in Table 5.

[0041]

[Table 5]

Also in this case, the composition of the present invention showed a remarkable improvement in elongation retention. On the other hand, when used in combination with hindered phenol, a slight coloring tendency was observed, but the coloring level was lower than that in the system containing hindered phenol alone.

[0043]

Continuation of the front page (56) References JP-A-1-172362 (JP, A) JP-B-47-17766 (JP, B1) JP-B-37-14223 (JP, B1) (58) Fields investigated (Int) .Cl. ⁷ , DB name) C08L 59/00-59/04

Claims (5)

(57) [Claims] (1) A compound represented by the general formula (I):
A stabilized polyoxymethylene resin composition containing about 5% by weight. Y ¹ -O-Ar ¹ -X-Ar ² -OY ² (I) wherein Ar ¹ and Ar ² represent an arylene group having no direct hydroxyl group and may be the same or different, and X is -C _p H _2p- , -C
_{m H 2m OC n H 2n -} , -C m H 2m SC n H 2n -, -C p H 2p N (C r H 2r + 1) C q H 2q -, - C p H 2p COC q H 2q - , -C _p H _2p COOC
_q H _2q- , -C _p H _2p CON (C _r H _{2r + 1} ) C _q H _2q- , -C _p H _2p S (= O) ₂ C _q H _2q- , -C _p H _2P P (= O) (R) C _q H _2q- , -C _p H _2p P (= O) (R) OC _q H _2q- , -C _p H
_2p OP (= O) (R) OC _q H _2q- (where m, n is an integer of 1 to 20, p, q, r is an integer of 0 to 20,
R is a divalent atomic group selected from C _{1 to} C ₂₀ alkyl, alkoxy groups or phenyl groups), and Y ¹ and Y ² are -C _m H _{2m + 1} ,-(C _m H _2m O) _n C _l H _{2l + 1} , -C _m H
_2m SC _p H _{2p + 1} , -C _m H _2m N (C _p H _{2p + 1} ) (C _q H _{2q + 1} ), -C _m H _2m COC _n H _{2n + 1} , -C _m H
_2m COOC _n H _{2n + 1} , -C _m H _2m OCOC _n H _{2n + 1} , -C _m H _2m CON (C _p H _{2p + 1} ) (C _q H _{2q + 1} ), -C _m H _2m N ( C _p H _{2p + 1} ) COC _q H _{2q + 1} , -C _m H _2m S (= O) ₂ C _n H _{2n + 1} , -C _m H _2m P (= O) (R) C _n H _{2n + 1} , -C _m H _2m P (= O) (R) OC _n H _{2n + 1} , -C _m H _2m OP (= O) (R) C _n H _{2n + 1} , -C _m H _2m OP (= O) (R) OC _n H _{2n + 1} (where m, n, l is an integer of 1 to 20, p, q is an integer of 0 to 20,
R represents one or more monovalent atomic groups selected from C _{1 to} C ₂₀ alkyl, alkoxy groups, or phenyl groups;
Y ¹ and Y ² may be the same or different. 2. In the general formula (I), X is -C _p H _2p- ,
_{-C m H 2m OC n H 2n} -, -C m H 2m SC n H 2n -, -C p H 2p N (C r H 2r + 1) C q H 2q -, - C p H 2p COC q H
_2q- , -C _p H _2p COOC _q H _2q- , -C _p H _2p S (= O) ₂ C _q H _2q- (where m, n are integers from 1 to 20, p, q, r are 0 (Integer of ~ 20)
The stabilized polyoxymethylene resin composition according to claim 1, comprising a divalent atomic group selected from the group consisting of: 3. In the general formula (I), Y ¹ or Y ² is
-C _m H _{2m + 1} ,-(C _m H _2m O) _n C _l H _{2l + 1} , -C _m H _2m COOC _n H _{2n + 1} , -C _m H _2m OCOC _n
H _{2n + 1} , -C _m H _2m N (C _p H _{2p + 1} ) (C _q H _{2q + 1} ) (where m, n, l is an integer of 1 to 20, p, q is an integer of 0 to 20 integer)
3. The stabilized polyoxymethylene resin composition according to claim 1, which is selected from the group consisting of: 4. In the general formula (I), Ar ¹ and Ar ² represent —X
-And other than -OY ¹ and -OY ² have no substituent, or
-C _m H _{2m + 1} ,-(C _m H _2m O) _n C _l H _{2l + 1} , -C _m H _2m SC _p H _{2p + 1} , -C _m H _2m COC _n H _{2n + 1} , -C _m H _2m COOC _n H
_{2n + 1} , -C _m H _2m OCOC _n H _{2n + 1} , -C _m H _2m S (= O) ₂ C _n H _{2n + 1} , -C _m H _2m P (=
O) (R) C _n H _{2n + 1} , -C _m H _2m P (= O) (R) OC _n H _{2n + 1} , -C _m H _2m OP (= O) (R) C _n H _{2n + 1} , -C _m H _2m OP (= O) (R) OC _n H _{2n + 1} , -C _m H _2m N (C _p H _{2p + 1} ) (C
_q H _{2q + 1} ), -C _m H _2m CON (C _p H _{2p + 1} ) (C _q H _{2q + 1} ), -C _m H _2m N (C _p H _{2p + 1} ) COC _q H
_{2q + 1} (where m, n, l are integers from 1 to 20, p, q are integers from 0 to 20,
R is an alkyl group of C ₁ -C _20, or a phenyl group) and a stabilizing polyoxymethylene resin according to any one of claims 1 to 3 is a benzene ring having as substituents the atomic group selected from a phenyl group Composition. 5. A phenolic compound, a nitrogen-containing compound, an alkali or alkaline earth metal, containing 0.01 to 5% by weight of the compound represented by the general formula (I) according to claim 1. A stabilized polyoxymethylene resin composition, which is used in combination with one or more of a hydroxide, an inorganic acid salt and a carboxylate.