JPH04331259A - Stabilized polyoxymethylene resin composition - Google Patents

Abstract

PURPOSE:To prepare the title compsn. excellent in thermal stability by incorporating a specified amt. of a specific compd. into the compsn. CONSTITUTION:0.01-5wt.% compd. of the formula: Ar(-O-X)s[wherein Ar is a benzene or naphthalene ring having no hydroxyl group directly attached; X is -CmH2m-1, -(CmH2mO)nCpH2p-1, -CmH2m-SCpH2p-1, -CmH2mN (CpH2p-1)(CqH2q-1), -CmH2mCOCnH2n-1, -CmH2mCOOCnH2n-1, -CmH2 mOCOCnH2n-1, -CmH2mCON(CpH2p-1)(CqH2q-1), -CmH2mN(CpH2p-1)COCq-1, -CmH2mS(=O)2CnH2n-1, -CmH2mP(=O)(R)Cn-H2n-1, -CmH2mP(=O)(R)OCnH2n-1, -CmH2mOP(=O)(R)CnH2n-1, -CmH2mOP(=O)(R)OCnH2n-1 (wherein (m) and (n) are each 1-20; (p) and (q) are each 0-20; and R is 1-20C alkyl, alkoxy, phenly, or phenoxy); and (s) is 2 or 3] is incorporated into the title compsn.

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 resistance stability and a composition thereof.

0002

[Prior Art and Problems to be Solved by the Invention] Polyoxymethylene resin has an excellent balance of various physical properties and is easy to process, so it is used as a representative engineering plastic for electrical/electronic parts, automobile parts, etc. It is widely used as a mechanical part. However, with the expansion and diversification of uses, demands for quality tend to become more sophisticated. Required characteristics include reduction in mechanical strength due to extrusion or molding processes, and deposits on molds, etc.
generation under long-term heating conditions (heat aging)
Examples include reduction in mechanical properties and suppression of discoloration of molded products to a low level. One of the important factors for these phenomena is the decomposition of the polymer upon heating.

[0003] Due to its chemical structure, polyoxymethylene inherently has the property of being easily decomposed under heated oxidizing atmosphere, acidic or alkaline conditions. To stabilize the chemically active ends, should the ends of the polymer be esterified by acetylation etc. (homopolymer)?
Alternatively, there is a method in which trioxane is copolymerized with a monomer having adjacent carbon bonds such as a cyclic ether or a cyclic formal during polymerization, and then the unstable end portion is decomposed and removed to form an inert stable end (copolymer). . However, during heating, cleavage and decomposition reactions also occur in the main chain portion of the polymer, and the above treatments alone cannot prevent this reaction; in practice, it is essential to add antioxidants and other stabilizers. There is.

However, even with polyoxymethylene compositions containing these stabilizers, decomposition of the polymer cannot be completely suppressed, and in fact, during molding, the action of heat and oxygen in the cylinder of the molding machine is and by main chain decomposition,
Alternatively, formaldehyde may be generated from the ends that are not sufficiently stabilized, worsening the working environment during extrusion molding, or when molding is performed for a long time, fine powder or tar-like materials may adhere to the mold surface (mold deposits). ), which is one of the biggest factors in reducing work efficiency and deteriorating the surface condition of molded products, and decomposition of the polymer causes a decrease in mechanical strength and discoloration of the resin. Furthermore, decomposition of the main chain when a molded product is heated for a long period of time (heat aging) also causes a decrease in mechanical strength, coloring, etc. Because of this, efforts continue to seek more effective stabilizer formulations.

[0005] Antioxidants added to polyoxymethylene resins include phenol compounds having sterically hindered groups (hindered phenols) or amine compounds having sterically hindered groups (hindered amines), and other stabilizers such as Compounds such as polyamides, urea derivatives, amidine compounds, alkali or alkaline earth metal hydroxides, and organic or inorganic acid salts are used in combination.

Hindered phenols are particularly effective as antioxidants, but on the other hand, phenols are weak acids;
Furthermore, since it becomes a strong acid by absorbing light, it can even become a polymer decomposition catalyst as the amount added increases. In addition, its oxidized form tends to become a coloring factor. Moreover, it may itself cause mold deposits during molding. Therefore, during molding, heat aging, or under light irradiation conditions, it functions as a stabilizer and at the same time causes decomposition of the polymer, so it is difficult to formulate a stabilizer formulation that has a good balance between molding stability, heat aging stability, and weather resistance. Although various proposals and efforts have been made so far, satisfactory results have not always been obtained.

The object of the present invention is to improve the stability of such polyoxymethylenes.

[0008]

[Means for Solving the Problems] The present inventors solved the above-mentioned problems, and as a result of searching and studying a more effective stabilizer for polyoxymethylene, the present inventors discovered that a phenoxy unit was added in the structure of the stabilizer. It has been discovered that a specific series of compounds containing the above compounds are effective as stabilizers for polyoxymethylene, leading to the present invention.

That is, the present invention relates to a polyoxymethylene resin composition characterized in that 0.01 to 5% by weight of a phenoxy compound represented by the general formula (I) is added to the polyoxymethylene resin. The purpose is to improve problems caused by the stability of the resin, such as deterioration of the resin due to oxidation or thermal decomposition during molding, generation of mold deposits, and deterioration during heat aging.

Ar(-O-X)s
(I) In general formula (I), Ar represents a benzene or naphthalene ring (excluding those having a directly bonded hydroxyl group as a substituent), and among these, a benzene ring is particularly preferred. -OX is a substituent other than hydroxyl group, i.e., as -
CmH2m+1 , -(CmH2mO)nCpH2p+
1, -CmH2mSCpH2p+1, -CmH2m
COCnH2n+1 , -CmH2mCOOCnH2n
+1, -CmH2mOCOCnH2n+1, -Cm
H2mCON (CpH2p+1) (CqH2q+1),
-CmH2mN (CpH2p+1) COCqH2q+1
, -CmH2mS(=O)2CnH2n+1 , -C
mH2mP(=O)(R)CnH2n+1, -CmH2
mP(=O)(R)OCnH2n+1, -CmH2m
OP(=O)(R)CnH2n+1, -CmH2mO
P(=O)(R)OCnH2n+1 (where m, n are integers from 1 to 20, p, q are integers from 0 to 20, R is C
1 to C20 alkyl, alkoxy group, or phenyl, phenoxy group). Among the above X, especially -C
mH2m+1, -(CmH2mO)nCpH2p+1
or hydroxyalkyl and its condensates, and -CmH2mCOOCnH2n+
1, -CmH2mOCOCnH2n+1, etc., or -CmH2mN (CpH2
Those having an amino group such as p+1) (CqH2q+1) are preferable, and for example, the alkyl group includes a straight-chain alkyl group,
Isopropyl group, isobutyl group, sec-butyl group, t
ert-butyl group, etc., as a hydroxyalkyl group, hydroxyethyl group, hydroxypropyl group, hydroxybutyl group, 3-hydroxy-2-methylpropyl group, 2
-Hydroxy-2-methylpropyl group, hydroxypentyl group, 3-hydroxy-2,2-dimethyl-propyl group, etc., and hydroxyalkyl group condensates such as ethylene glycol, propanediol, 1,4-butanediol, etc. Examples include condensates.

On the other hand, s indicates the number of substitutions in the above alkoxy derivative; for example, when Ar is a benzene ring, it is allowed to be 2 to 6, and when it is a naphthalene ring, it is allowed to be 2 to 8, but preferably 2.
Or 3. Further, the plurality of alkoxy derivatives do not need to be of the same type, and may be of different types. Moreover, the relative substitution position may be any of the o-, m-, and p-positions.

These aromatic rings (Ar) are unsubstituted other than -OX, or have substituents other than -OX, for example,
-CmH2m+1, -(CmH2mO)nCpH2p
+1, -CmH2mSCpH2p+1, -CmH2
mN (CpH2p+1) (CqH2q+1), -CmH
2mCOCnH2n+1 , -CmH2mCOOCnH
2n+1 , -CmH2mOCOCnH2n+1 , -
CmH2mCON (CpH2p+1) (CqH2q+1
), -CmH2mN (CpH2p+1) COCnH2n
+1, -CmH2mS(=O)2CnH2n+1,
-CmH2mP(=O)(R)CnH2n+1, -Cm
H2mP(=O)(R)OCnH2n+1, -CmH
2mOP(=O)(R)CnH2n+1, -CmH2
mOP(=O)(R)OCnH2n+1 (where, m, n are integers of 1 to 20, p, q are 0 to 2
The integer of 0, R may be a C1-C20 alkyl, alkoxy group, phenyl, phenoxy group), and a substituent selected from a phenyl group, and among them, except -OX may be unsubstituted or a substituent. -CmH2m
+1, -(CmH2mO)nCpH2p+1, -C
mH2mCOOCnH2n+1 , -CmH2mCON
(CpH2p+1) (CqH2q+1) is preferably used. When such a substituent is present, it increases the reactivity of the compound, improves the compatibility with polyoxymethylene resin, or increases the boiling point and sublimation temperature to prevent these stabilizers from volatilizing at high temperatures. It is effective. These substituents are not limited to one, but a plurality or two or more types may be introduced, and the substitution position may be o-, m-, or p-.

These compounds of formula (I) are contained in an amount of 0.01 to 5% by weight, preferably 0.1% by weight based on the polyoxymethylene resin.
~2% by weight is added. If the amount of these compounds added is too small, the stabilizing effect will be poor, while if it is too much, the decomposition or discoloration of the polymer may be accelerated, which is not preferable.

[0014] The polyoxymethylene to which these additives are blended is a polymer compound whose main constituent unit is an oxymethylene group, and is a polyoxymethylene homopolymer or a polyoxymethylene homopolymer or a polyoxymethylene compound containing a small amount of other constituent units in addition to the oxymethylene group. The polymer may be a copolymer, a terpolymer, or a block copolymer, and the molecules may not only be linear but may also have a branched or crosslinked structure. Further, there is no particular restriction on the degree of polymerization, and any degree may be used as long as it can be molded.

A remarkable stabilizing effect can be seen even when the above compound is used alone, but in addition, nitrogen-containing compounds such as amines and amides, alkali or alkaline earth metal hydroxides, inorganic acid salts, carboxylic acid salts or It is also possible to use one or more metal-containing compounds such as alkoxides and sterically hindered phenol compounds.

[0016] Here, the nitrogen-containing compounds include nylon 12,
Single or copolymerized polyamides such as nylon 6/12 and nylon 6/66/610, substituted polyamides having methylol groups, etc., nylon salts, polyamides such as polyesteramide synthesized from a combination with caprolactam, polyaminotriazole, dicarbonate Acid dihydrazide, thermal condensates synthesized from urea by heating, 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''-trimethylolmelamine, benzoguanamine, 2,4-diamino-6-methyl-sym-triazine, 2,4-diamino-6-butyl-sym-triazine, 2,4-diamino-6-benzyloxy -sy
m-triazine, 2,4-diamino-6-butoxy-
sym -triazine, 2,4-diamino-6-cyclohexyl-sym -triazine, 2,4-diamino-
6-chloro-sym-triazine, 2,4-diamino-6-mercapto-sym-triazine, 2,4-dioxy-6-amino-sym-triazine (amelide), 2-oxy-4,6-diamino-sym -triazine (ameline), N,N,N',N'-tetracyanoethylbenzoguanamine, and the like. Also included are hindered amines described below.

[0017] Metal compounds include hydroxides, carbonates, phosphates, silicates, borates, etc. of sodium, potassium, magnesium, calcium or barium;
Carboxylate salts such as oxalates, malonates, succinates, adipates etc., higher (C) salts such as stearates etc.
10-C32) fatty acid salts and salts of substituted higher fatty acids having substituents such as hydroxyl groups. Furthermore, basic compounds containing at least one tertiary nitrogen atom and a metal carboxylic acid in the same molecule, such as sodium N-methyliminodiacetate, trisodium nitrilotriacetate,
Ethylenediaminetetraacetic acid tetrasodium, ethylenediaminetetraacetic acid dicalcium, diethylenetriaminepentaacetic acid 5
Examples include sodium, pentapotassium diethylene pentaacetate, hexasodium triethylenetetraminehexaacetate, sodium ethyleneoxybis(ethylamine)-N,N,N',N'-4acetate, and the like.

In addition, when the compound of formula (I) in the present invention is used in combination with a known antioxidant, such as hindered phenol or hindered amine, it exhibits remarkable synergistic effects in further improving thermal stability, especially in improving heat aging properties, etc. The effect is recognized.

Examples of hindered phenolic antioxidants used in combination for this purpose include 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'- Examples include hexamethylenebis(3,5-di-tert-butyl-4-hydroxy-hydrocinnamide).

Further, the hindered amine compound is a piperidine derivative having a sterically hindered group, examples of which include 4-acetoxy-2,2,6,6-tetramethylpiperidine, 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, bis(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, high molecular weight piperidine derivative heavy condensates, such as dimethyl succinate-1-(2
-hydroxyethyl)-4-hydroxy-2,2,6,
6-tetramethylpiperidine polycondensates and the like are also effective.

[0021] The composition of the present invention also includes:
Or, in order to impart properties to the molded product according to the purpose, general additives for thermoplastic resins, such as colorants such as dyes and pigments, lubricants, nucleating agents, mold release agents, antistatic agents and other surfactants, Alternatively, one or more types of organic polymer materials, inorganic or organic fibrous, powdery, or plate-like fillers can be added.

[0022] The method for preparing the composition of the present invention is not particularly limited; for example, simply blending well is effective.
After mixing each component, the mixture may be melt-kneaded and extruded using an extruder or the like to form pellets, which may then be molded. In addition, a method in which pellets with different compositions are prepared, a predetermined amount of the pellets are mixed and molded, and a molded product having the desired composition is obtained after molding, or a method in which one or more of each component is directly charged into a molding machine; Either can be used. Furthermore, in order to make the blend of additives uniform, it is an effective method to add a part of the resin component as a fine powder and mix it with other components.

Furthermore, 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]

Effects of the Invention As shown in the above explanations and examples, the compound of formula (I) according to the present invention itself does not contain any acidic elements and does not easily become a coloring substance. Resin compositions are highly effective in suppressing polymer decomposition during molding, preventing the generation of decomposed gas, suppressing the decrease in the degree of polymerization and the accompanying decrease in mechanical strength, suppressing the generation of mold deposits, and preventing discoloration. To provide a polyoxymethylene resin or a composition thereof, which is not only effective in preventing a decrease in mechanical strength and discoloration during heat aging, but also in improving weather resistance, and has well-balanced thermal stability. It is something.

[0025]

[Example] In order to specifically demonstrate the effects of the present invention,
Although the present invention will be described with reference to examples, the present invention is not limited to these examples in any way.

Examples 1-6, Comparative Examples 1-2 Examples 1-6
Take 100 parts of a polyoxymethylene copolymer resin that does not contain any stabilizer, grind it, and add the following compounds (A) to (F), respectively.

[0027]

[Chemical formula 1]

[0028] 0.3 parts by weight of each was added and mixed well with stirring under a nitrogen atmosphere. In order to evaluate the degree of decomposition of the polymer main chain by the change in melt viscosity over time as the molecular weight decreases, 10 g of this mixture was put into a Takara Kogyo MX101 type melt indexer, and after melting and residence at 210 ° C. for a predetermined time. , through an orifice with an inner diameter of 2.09 mm, 2.1
The weight of resin flowing out per 10 minutes (MI value) was measured while applying a load of 6 kg. The measurement was carried out after 7 minutes, 30 minutes, and 60 minutes of residence after resin injection, and the increase in MI value after 60 minutes, ΔMI = MI
(60 minutes)-MI (7 minutes) was determined. For comparison,
Polyoxymethylene copolymer resin without any additives, and pentaerythritol-tetrakis [3-
(3,5-di-tert-butyl-4-hydroxyphenyl)propionate] (Irganox 1010
, manufactured by Ciba Geigy) was similarly added to 100 parts by weight of polyoxymethylene copolymer resin and the same measurements were conducted (Comparative Examples 1 and 2, respectively). The results are shown in Table 1.

[0029]

[Table 1]

[0030] By adding a phenoxy compound, the initial MI
Although there were some cases where the value increased, this was probably due to the lubricating effect of the additive, and was due to a mechanism different from the decomposition of the polymer. The increase in the MI value of the composition of the present invention after 30 minutes is small, and the decomposition of the polymer chains is extremely efficiently suppressed. Furthermore, the increase (ΔMI) after 60 minutes is extremely small.

Examples 7 to 12, Comparative Examples 3 to 4 Examples 1 to 4
The polyoxymethylene copolymer resin and additives (A) to (F) were blended according to the same recipe as in 6, and then 2
The mixture was melt-kneaded and extruded using an extruder at 00°C to form pellets. After melting and retaining 8 g of these pellets at 200°C for 5 minutes in a melt indexer, a load was applied to allow them to flow out, and the formaldehyde generated was collected and measured using the acetylacetone method. It was expressed as the weight of formaldehyde generated (ppm). For comparison, the same procedure was conducted for a case in which no additive was added (Comparative Example 3) and a case in which Irganox 1010 was similarly blended (Comparative Example 4).

[0032] Also, using these pellets, they were kept in an injection molding machine at a temperature of 200°C for 1 hour, and then 40 m
A plate-shaped molded product of m x 70 mm x 2 mm was molded, and the coloring due to melt retention was measured using a Z-1001DP color difference meter manufactured by Nippon Denshoku Industries Co., Ltd., and the degree of yellowness (JIS K7103) was measured. Furthermore, these pellets were injection molded at a cylinder temperature of 200°C to form a plate-shaped molded product of 40 mm x 70 mm x 2 mm and JIS K7113 No. 1 type (thickness 3 mm).
) A tensile test piece was created. This molded product was heated to 140℃
After being left for 8 days (heat aging), the retention rate of tensile elongation was measured using a tensile test piece, and the coloration (yellowness indication) was measured using a plate-shaped molded product. These results are summarized in Table 2.
Shown below.

[0033]

[Table 2]

The composition of the present invention (Example) has a significantly reduced amount of formaldehyde generation, significantly less coloration during melt retention, and is also effective in improving elongation retention after heat aging and preventing coloration. It was seen.

Examples 13 to 18, Comparative Examples 5 to 8 The above compounds (A) or (B) were added in amounts of 0.1, 1, and 2, respectively, to 100 parts by weight of polyoxymethylene copolymer resin containing no additives. Added parts by weight, Example 1~
The same evaluation as in No. 12 was conducted. For comparison, 0.005 and 10 parts by weight of each additive were added to 100 parts by weight of the polyoxymethylene copolymer resin and evaluated in the same manner. These results are shown in Table 3.

[0036]

[Table 3]

Favorable results were obtained when the amount added was within the range of the present invention, but adding 0.005 parts by weight had little effect on polymer decomposition, gas generation, and elongation retention, while adding 10 parts by weight When added, the coloration was greater.

Examples 19 to 24, Comparative Example 9 Compounds (A) to (F) shown in Examples 1 to 6 were added to 100 parts by weight of a polyoxymethylene copolymer resin containing no additives.
) and 0.3 parts by weight each, and melamine
0.2 parts by weight was added and evaluated in the same manner as Examples 1 to 12. As a comparative example, a similar evaluation was conducted for a case in which only 0.2 parts by weight of melamine was added. The results are shown in Table 4.

[0039]

[Table 4]

In this case as well, the composition of the present invention was found to have further improved effects in terms of inhibiting formaldehyde gas generation, maintaining elongation after heat aging, etc.

Examples 25 to 32, Comparative Examples 10 to 11 Among the compounds shown in Examples 1 to 6, (A), (B), (C
) and (D), and phenolic antioxidant Irganox 1010 or hindered amine antioxidant bis(2,2,
6,6-tetramethyl-4-piperidyl) sebacate (
Sanol LS-770, manufactured by Sankyo Co., Ltd.) each 0.2
Parts by weight, and further 0.2 parts by weight of melamine were added to 100 parts by weight of polyoxymethylene copolymer resin, and the same evaluations as in Examples 1 to 12 were performed. As a comparative example, I
0.4 parts by weight of rganox 1010 and 0.2 parts by weight of melamine (Comparative Example 10), or Sanol
0.4 parts by weight of LS-770 and 0.2 parts by weight of melamine (Comparative Example 11) were added and evaluated in the same manner as in the examples. The results are summarized in Table 5.

[0042]

[Table 5]

In this case as well, 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 tendency towards coloring was observed, but the level of coloring was lower compared to the system in which only hindered phenol was added.

Claims (5)

[Claims] Claim 1: A compound represented by the general formula (I), containing 0
．． A stabilized polyoxymethylene resin composition containing 01 to 5% by weight. Ar(-O-X)s
(I) Ar represents a benzene or naphthalene ring (excluding those having a directly bonded hydroxyl group as a substituent),
is -CmH2m+1, -(CmH2mO)nCpH2
p+1, -CmH2mSCpH2p+1, -CmH
2mN (CpH2p+1) (CqH2q+1), -Cm
H2mCOCnH2n+1 , -CmH2mCOOCn
H2n+1 , -CmH2mOCOCnH2n+1 ,
-CmH2mCON (CpH2p+1) (CqH2q+
1), -CmH2mN (CpH2p+1) COCqH2
q+1 , -CmH2mS(=O)2CnH2n+1
, -CmH2mP(=O)(R)CnH2n+1, -C
mH2mP(=O)(R)OCnH2n+1, -Cm
H2mOP(=O)(R)CnH2n+1, -CmH
2mOP(=O)(R)OCnH2n+1 (however, m,
n is an integer of 1 to 20, p, q are integers of 0 to 20, R
is an atomic group selected from C1 to C20 alkyl, alkoxy groups, phenyl, phenoxy groups,
s is an integer of 2 or 3. 2. The stabilized polyoxy as claimed in claim 1, wherein in the compound represented by the general formula (I), Ar is a benzene ring (excluding those having a directly bonded hydroxyl group as a substituent), and s is 2. Methylene resin composition. Claim 3: In general formula (I), X is -Cm
H2m+1, -(CmH2mO)nCpH2p+1
, -CmH2mCOOCnH2n+1 , -CmH2m
OCOCnH2n+1 , -CmH2mN (CpH2p
+1) (CqH2q+1) (However, m, n are 1 to 20
The stabilized polyoxymethylene resin composition according to claim 1 or 2, wherein p and q are integers of 0 to 20. 4. In general formula (I), Ar is -OX
Others are unsubstituted or -CmH2m+1, -(
CmH2mO)nCpH2p+1, -CmH2mSC
pH2p+1, -CmH2mCOCnH2n+1,
-CmH2mCOOCnH2n+1, -CmH2mO
COCnH2n+1, -CmH2mS(=O)2Cn
H2n+1, -CmH2mP(=O)(R)CnH2
n+1, -CmH2mP(=O)(R)OCnH2n+
1, -CmH2mOP(=O)(R)CnH2n+1
, -CmH2mOP(=O)(R)OCnH2n+1
, -CmH2mN (CpH2p+1) (CqH2q+1
), -CmH2mCON(CpH2p+1)(CqH2
q+1), -CmH2mN(CpH2p+1)COCn
H2n+1 (where m, n are integers from 1 to 20, p, q are 0 to 2
4. The stable compound according to claim 1, wherein R is a benzene ring having as a substituent an atomic group selected from C1 to C20 alkyl, alkoxy groups, phenyl, phenoxy groups, and phenyl groups. polyoxymethylene resin composition. 5. Contains 0.01 to 5% by weight of the compound represented by the general formula (I) according to any one of claims 1 to 4, and further contains a phenolic compound, a nitrogen-containing compound, an alkali or an alkaline earth. A stabilized polyoxymethylene resin composition containing one or more of metal hydroxides, inorganic acid salts, and carboxylic acid salts.